Category: 13194-68-8

These common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 4-Iodo-2-methylaniline

General procedure: Aniline derivative (1 eq) was mixed with iced water and/or absolute EtOH (2 mL by mmol of reagent) and stirred at 0 C then hydrochloric acid 37% (4 eq) was added dropwise rapidly. Sodium nitrite (1.1 eq or 1.3 eq aniline substituent depending) was added solid or in solution (H2O/EtOH 1 M) and the reaction mixture was stirred at 0-2 C for 30 min. The solvent was removed carefully under reduced pressure without heating and can be used without further purification. 5-Amino-4-hydroxynaphtalene-2,7-disulfonic acid sodium salt (0.9 eq) was dissolved in iced water (5 mL by mmol of reagent) then pH was adjusted to 9 by adding 30% NaOH solution. The diazonium salt was added to the naphthalene moiety and pH maintained at 9 by addition of 10% NaOH solution. After complete addition of the diazonium salt to the 5-amino-4-hydroxynaphthalene-2,7-disulfonic acid monosodium salt, stirring was maintained at 0 C for 2 h. Degraded diazonium was removed after extraction with EtOAc and water soluble diazo compounds were recrystallized three times from EtOH/(H2O; pH 2) (1/1). All organic impurities were then extracted by washing with small portions of Et2O. The precipitated compounds were dried under vacuum.

The synthetic route of 4-Iodo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Favre-Besse, Franck-Cyril; Poirel, Odile; Bersot, Tiphaine; Kim-Grellier, Elodie; Daumas, Stephanie; El Mestikawy, Salah; Acher, Francine C.; Pietrancosta, Nicolas; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 236 – 247;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13194-68-8, name is 4-Iodo-2-methylaniline, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

(a) Preparation of 4Fluoro-2-(4iodo-2-methyl-phenylamino)-benzoic acid To a stirred solution containing 3.16 g (0.0133 mol) of 2-amino-5-iodotoluene in 5 mL of tetrahydrofuran at -78 C. was added 10 mL (0.020 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 15 minutes, after which time a solution of 1.00 g (0.00632 mol) of 2,4-difluorobenzoic acid in 10 mL of tetrahydrofuran was added. The reaction temperature was allowed to increase slowly to room temperature, at which temperature the mixture was stirred for 2 days. The reaction mixture was concentrated by evaporation of the solvent under reduced pressure. Aqueous HCI (10%) was added to the concentrate, and the solution was extracted with dichloromethane. The organic phase was dried (MgSO4) and then concentrated over a steambath to low volume (10 mL) and cooled to room temperature. The off-white fibers which formed were collected by vacuum filtration, rinsed with hexane, and dried in a vacuum-oven (76 C.; ca. 10 mm of Hg) to afford 1.10 g (47%) of the desired material; mp 224-229.5 C.; 1H NMR (400 MHz, DMSO): delta 9.72 (s, 1H), 7.97 (dd, 1H, J=7.0, 8.7 Hz), 7.70 (d, 1H, J=1.5 Hz), 7.57 (dd, 1H,.J=8.4, 1.9 Hz), 7.17 (d, 1H, J=8.2 Hz), 6.61-6.53 (m, 2H), 2.18 (s, 3H); 13C NMR (100 MHz, DMSO): delta 169.87, 166.36 (d, JC-F=249.4 Hz), 150.11 (d, JC-F=11.4 Hz), 139.83, 138.49, 136.07, 135.26 (d, JC-F=11.5 Hz), 135.07, 125.60, 109.32, 104.98 (d, JC-F=21.1 Hz), 99.54 (d, JC-F=26.0 Hz), 89.43, 17.52; 19F NMR (376 MHz, DMSO): delta104.00 to -104.07 (m); IR (KBr) 1670 (C=O stretch)cm-1; MS (CI) M+1=372.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Related Products of 13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-iodo-2-methylbenzenamine 24 (233 mg, 1 mmol) on reaction with 1-tert-butyl-4-ethynylbenzene (25b, 158 mg, 1 mmol) by employing Sonagashira coupling conditions using Pd(PPh3)4 (69.3 mg, 0.06 equiv) as catalyst, Cul (22.8 mg, 0.12 equiv) as cocatalyst, butyl amine (261 mg, 3 equiv) as base and ether as solvent and kept the reaction for 6 h. After completion of the reaction as indicated by TLC and the reaction mixture is extracted into ether (4×25 mL) from the aqueous layer and concentrated in vacuo. The compound was further purified by column chromatography using 60-120 silica gel (ethyl acetate/hexane,1:9) to obtain 4-((4-tert-butylphenyl) ethynyl)-2-methyl benzene amine (26b) as pure product. Anthranilic acid (27, 137 mg, lmmol) on reaction with acetic anhydride at 150 C. and reflux for 30 min, after completion of reaction aqueous sodium bicarbonate solution is added and extracted in ethyl acetate (4×25 mL) from the aqueous layer and concentrated in vacuo afforded 2-methyl 4H-benzo[d][1,3]oxazin-4-one compound ( 28) as pure product. To a stirred solution of 4-((4-tertbutylphenyl)ethynyl)-2-methylbenzenamine (26b, 263 mg, 1 mmol) with 2-methyl-4H-benzo[d][1,3]oxazin-4-one (28, 161 mg, 1 mmol) in acetic acid and reflux for 8 h After completion of the reaction as indicated by TLC. then the reaction mixture was quenched with NaHCO3 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2SO4 afforded 3-(4-((4-tert-butylphenyl)ethynyl)-2-methylphenyl)-2-methylquinazolin-4(3H)-one (29b). Reaction of 3-(4-((4-tert-butylphenyl)ethynyl)-2-methylphenyl)-2-methylquinazolin-4(3H)-one (29b, 406 mg, 1 mmol) with 2,4-dihydroxybenzaldehyde (30d, 138 mg, 1 mmol) was taken in acetic acid Then the resulting mixture was stirred under reflux conditions for 8 h and then the reaction mixture was quenched with NaHCO3 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2SO4.The resulting product ( 5d) was purified by column chromatography employing EtOAc/Hexane as an eluent.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Electric Literature of 13194-68-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13194-68-8, name is 4-Iodo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-ethynyl-2-methyl-benzene (70 mg, 602.62 mumol, 75.92 muL, 1 eq), 4-iodo-2-methyl-aniline (140.44 mg, 602.62 mumol, 1 eq), CuI (22.95 mg, 120.52 mumol, 0.2 eq), Pd(PPh3)4 (69.64 mg, 60.26 mumol, 0.1 eq) and butan-1-amine (132.23 mg, 1.81 mmol, 178.68 uL, 3 eq) in THF (5 mL) was degassed and purged with N2 for 3 times. The mixture was stirred at 20 C. for 16 h under N2. The reaction mixture was quenched by addition of water (50 mL), extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified by flash silica gel chromatography (from PE/EtOAc=1/0 to 5/1, TLC: PE/EtOAc=5/1, Rf=0.23) to yield 2-methyl-4-[2-(o-tolyl)ethynyl]aniline (100 mg, 451.88 mumol, 75.0% yield, 100% purity) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.50-7.43 (m, 1H), 7.27-7.12 (m, 5H), 6.65 (d, J=8.2 Hz, 1H), 3.78 (s, 2H), 2.51 (s, 3H), 2.18 (s, 3H); ES-LCMS m/z 222.2 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Iodo-2-methylaniline. I believe this compound will play a more active role in future production and life.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13194-68-8, name is 4-Iodo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., category: iodides-buliding-blocks

(b) Preparation of 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid To a stirred solution comprised of 1.88 g (0.00791 mol) of 2-amino-5-iodotoluene in 10 mL of tetrahydrofuran at -78 C. was added 6 mL (0.012 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 10 minutes, after which time a solution of 1.00 g (0.00392 mol) of 5-bromo-2,3,4-trifluorobenzoic acid in 15 mL of tetrahydrofuran was added. The cold bath was subsequently removed, and the reaction mixture stirred for 18 hours. The mixture was concentrated, and the concentrate was treated with 100 mL of dilute (10%) aqueous hydrochloric acid. The resulting suspension was extracted with ether (2*150 mL), and the combined organic extractions were dried (MgSO4) and concentrated in vacuo to give an orange solid. The solid was triturated with boiling dichloromethane, cooled to ambient temperature, and collected by filtration. The solid was rinsed with dichloromethane, and dried in the vacuum-oven (80 C.) to afford 1.39 g (76%) of a yellow-green powder; mp 259.5-262 C.; 1H NMR (400 MHz, DMSO): delta9.03 (s, 1H), 7.99 (dd, 1H, J=7.5, 1.9 Hz), 7.57 (dd, 1H, J=1.5 Hz), 7.42 (dd, 1H, J=8.4, 1.9 Hz), 6.70 (dd, 1H, J=8.4, 6.0 Hz), 2.24 (s, 3H); 19F NMR (376 MHz, DMSO): delta-123.40 to -123.47 (m); -139.00 to -139.14 (m); IR (KBr) 1667 (C=O stretch)cm-1; MS (CI) M+1=469. Analysis calculated for C14H9BrF2INO2: C, 35.93; H, 1.94; N, 2.99; Br, 17.07; F, 8.12; I, 27.11. Found: C, 36.15; H, 1.91; N, 2.70; Br, 16.40; F, 8.46; I, 26.05.

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 4-Iodo-2-methylaniline

Compound E (e.g., 4.3mmol) was added in ethyl acetate (e.g., 30mL), water (e.g., 30mL) and sodium hydroxide (e.g., 4.8mmol) were added and the resulting product was used for the subsequent reaction. 2, 2, 2-trichloroethyl chloroformate (e.g., 4.7mmol) was added dropwise to the above solution at 0-5C .Aftercompletionofdropping, the reaction was carried out at room temperature for 1 hour. The organic phase was separated, dried and concentrated under reduced pressure to obtain compound F, the yield was >95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13194-68-8, its application will become more common.

Reference:
Patent; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; SHI, Ying; MI, Yi; YANG, Hanyu; WANG, Xuliang; GONG, Denghuang; BAI, Min; CHEN, Xiaozhuo; CHEN, Yujie; ZHANG, Xuejiao; MA, Yuxiu; GAO, Qingzhi; (77 pag.)EP3357916; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 13194-68-8, The chemical industry reduces the impact on the environment during synthesis 13194-68-8, name is 4-Iodo-2-methylaniline, I believe this compound will play a more active role in future production and life.

To 4-iodo-2-methylaniline (23.3g) (available from Fluorochem) in ice (6Og) and concentrated hydrochloric acid (30ml) was added a solution of sodium nitrite (7.05g) in water (18ml) slowly with stirring over 20min, keeping the temperature below 50C. The mixture was allowed to stand at 0-50C for 2h, then added slowly at 0-50C over 30min to a mixture of diethyl malonate (17ml), ethanol (300ml) and water (50ml) containing sodium acetate (18.8g). The mixture was stirred for 2h at 0-50C then for 2h at 210C. The mixture was concentrated in vacuo to a volume of about 200ml, and the product was collected by filtration, washed with water (200ml) and dried under vacuum to give the title compound as a brown solid (28.9g). LC/MS Rt 3.85min m/z 405 [MH+].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Iodo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/45861; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13194-68-8, name is 4-Iodo-2-methylaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Iodo-2-methylaniline

(a) Preparation of 4-Fluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid To a stirred solution containing 3.16 g (0.0133 mol) of 2-amino-5-iodotoluene in 5 mL of tetrahydrofuran at -78 C. was added 10 mL (0.020 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 15 minutes, after which time a solution of 1.00 g (0.00632 mol) of 2,4-difluorobenzoic acid in 10 mL of tetrahydrofuran was added. The reaction temperature was allowed to increase slowly to room temperature, at which temperature the mixture was stirred for 2 days. The reaction mixture was concentrated by evaporation of the solvent under reduced pressure. Aqueous HCl (10%) was added to the concentrate, and the solution was extracted with dichloromethane. The organic phase was dried (MgSO4) and then concentrated over a steambath to low volume (10 mL) and cooled to room temperature. The off-white fibers which formed were collected by vacuum filtration, rinsed with hexane, and dried in a vacuum-oven (76 C.; ca. 10 mm of Hg) to afford 1.10 g (47%) of the desired material; mp 224-229.5 C.; 1H NMR (400 MHz, DMSO): delta 9.72 (s, 1H), 7.97 (dd, 1H, J=7.0, 8.7 Hz), 7.70 (d, 1H, J=1.5 Hz), 7.57 (dd, 1H, J=8.4, 1.9 Hz), 7.17 (d, 1H, J=8.2 Hz), 6.61-6.53 (m, 2H), 2.18 (s, 3H); 13C NMR (100 MHz, DMSO): delta 169.87, 166.36 (d,JC-F=249.4 Hz), 150.11 (d, JC-F=11.4 Hz), 139.83, 138.49, 136.07, 135.26 (d,JC-F=11.5 Hz), 135.07, 125.60, 109.32, 104.98 (d, JC-F=21.1 Hz), 99.54 (d, JC-F=26.0 Hz), 89.43, 17.52; 19F NMR (376 MHz, DMSO): delta-104.00 to -104.07 (m); IR (KBr) 1670 (C=O stretch)cm-1; MS (CI) M+1=372. Analysis calculated for C14H11FINO2: C, 45.31; H, 2.99; N, 3.77. Found: C, 45.21; H, 2.77; N, 3.64.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Gowan, Richard Carleton; Sebolt-Leopold, Judith; US2004/171632; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13194-68-8, name is 4-Iodo-2-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8IN

To a solution of 4-iodo-2-methyl-aniline (4.0 g, 17 mmol) and Pd (dppf) 2Cl 2 (140 mg, 0.17 mmol) in THF (50 mL) was added isopropylmagnisium chloride (25.5 mL, 51.0 mmol) at -78 and was reacted at reflux for 4 h. The reaction was quenched with a saturated solution of NH 4Cl, extracted with EtOAc, dried over anhydrous Na 2SO 4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a brown solid (320 mg, 12%). MS (ESI) : mass calcd. for C 10H 15N, 149.1 m/z found, 150.0 [M+H] +.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (999 pag.)WO2018/103058; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-methylaniline, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13194-68-8, Recommanded Product: 13194-68-8

First, N-(4-(2,5-bicyclo[2.2.1]heptenyl)-2-methylphenyl)maleimide was synthesized in two stages. 4-Iodo-2-methylaniline (5.33 g, 22.9 mmol) was dissolved in diethyl ether (20 mL), and slowly added dropwise at 0 C. to a diethyl ether solution (20 mL) of maleic anhydride (1.87 g, 19.1 mmol) in a nitrogen atmosphere. After stirring for two hours thereafter at room temperature, the precipitated solid was filtered out and washed with diethyl ether. The solid filtered out and sodium acetate (302 mg) were dissolved in acetic anhydride (30 mL) and stirred for three hours at 140 C. The solvent was distilled off under reduced pressure, water was added, and the solution was extracted by methylene chloride. The organic layer was dried using anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using chloroform-hexane mixed solvent (mixture ratio 1:1) as the developing solvent, and N-(4-iodo-2-methylphenyl)maleimide (4.20 g, 13.4 mmol, 74%) was obtained as a white solid. The spectral data of N-(4-iodo-2-methylphenyl)maleimide were as follows. (0129) 1H NMR (400 MHz, CDCl3): delta 7.70 (s, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.87 (s, 1H), 6.84 (d, J=8.4 Hz, 1H), 2.11 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 169.0, 140.0, 138.8, 136.0, 134.4, 130.3, 129.8, 95.1, 17.6; HRMS (APCI, positive): [M+] calcd. for C11H8INO2, 312.9600; found 312.9606.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Japan Science and Technology Agency; Yabu, Hiroshi; Saito, Yuta; Saito, Shohei; Yamaguchi, Shigehiro; Nobusue, Shunpei; (47 pag.)US10442886; (2019); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com