Category: 77317-55-6

Electric Literature of 77317-55-6,Some common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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.

To a solution of 4-fluorobenzyl zinc chloride (0.5M solution in THF, 27.ImL, 13.55mmol) was added PdCl2(dppf)CH2Cl2 (221mg, 0.27mmoL) and the solution was stirred for 5 minutes. To the solution was added 5-iodoanthranilic acid methyl ester (1.5g, 5.4mmol) and the solution was heated to 70 0C for 1 hour. Allowed to cool, quenched with saturated NH4CI, followed by saturated aqueous Na2EDTA, the solution was extracted with CH2CI2, dried (MgSO4), filtered, and concentrated to yield compound 102 A (1.4g, 100%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-iodobenzoate, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2009/143049; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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 77317-55-6, Computed Properties of C8H8INO2

To a solution of methyl anthranilate (7.75 g, 51.3 mmol, Aldrich) in DMF [(50] [ML)] was added NIS (11. [5] g, [51.] 3 mmol, Aldrich). The solution was stirred for 63 hours before being added to a separatory funnel with 200 mL of MTBE and washed with 5 X 200 mL of water. The organics were dried over MgS04 and evaporated yielding 13.8 g of tan solid as methyl [2-AMINO-5-IODOBENZOATE.] A mixture of methyl 2-amino-5- iodobenzoate (3.13 g, 11.3 mmol) and tetrakis (triphenylphosphine) palladium [(0)] (282 mg, 0.244 mmol, Strem) was placed under 1 atm of CO. THF (20 mL) was added, [ANDTHE SOLUTIONWAS HEATEDTO 60 C. TRI-N-BUTYLTINHYDRIDE] (3.7 mL, 12.7 mmol, Aldrich) was added dropwise with rapid stirring over 4 hours. The dark orange solution was heated a further 45 minutes and then added to a separatory funnel with [150] mL of EtOAc. This solution was washed with 2 X [150] mL of saturated aqueous NaHCO3 followed by 100 mL of brine. It was dried over MgS04 and evaporated leaving a brown oil that was purified by chromatography using a Biotage Flash 40 M silica cartridge with a gradient from [CHUCK] to 5% EtOAc in [CHZCLZ] as eluent. This chromatography failed to remove all of the tin, so the product was re- chromatographed using a Biotage Flash 40 M silica cartridge with 5% EtOAc in [CHUCK] as eluent. Yield was 863 mg of white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 77317-55-6 as follows. Formula: C8H8INO2

To a round bottom flask was added methyl 2-amino-5-iodobenzoate (5.00 g, 18.1 mmol) and di-tert-butyl dicarbonate (3.94 g, 18.1 mmol). The flask was sealed and evacuated/backfilled with nitrogen (3x) . Tetrahydrofuran (90 ml_) was added, and the reaction mixture was heated to 60 C overnight. 4-Dimethylaminopyridine (1.10 g, 9.02 mmol) was added, and the reaction mixture was heated for 1.5 hours. The reaction mixture was cooled to room temperature. Ethyl acetate and water were added, and the layers were separated . The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using ethyl acetate/hexanes as eluent provided the title compound as a pale yellow solid ( 1.70 g, 20%) : *H NMR (400 MHz, CDCI3) delta 8.32 (d, J = 2.1 Hz, 1H), 7.84 (dd, J = 8.3, 2.2 Hz, 1H), 6.93 (d, J = 8.3 Hz, 1H), 3.87 (s, 3H), 1.38 (s, 18H) ; EIMS m/z 478 ([M + H]+) .

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; SPARKS, Thomas C.; DEMETER, David A.; (242 pag.)WO2017/40742; (2017); 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 2-amino-5-iodobenzoate

General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv), bispinacolatodiboron (254 mg, 1 mmol, 2 equiv), and the appropriate aryl iodide (0.5 mmol). Under an argon atmosphere, freshly distilled DMSO (0.4 mL) and pyridine (0.4 to 1 equiv) were added successively using a syringe. The reaction mixture was heated to 105 C and stirred and stirred for 2 h under argon.

The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pinet, Sandra; Liautard, Virginie; Debiais, Megane; Pucheault, Mathieu; Synthesis; vol. 49; 21; (2017); p. 4759 – 4768;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 7 Synthesis of Nl-ethyloxycarbonyl-N2-allyl-5-(3- hydroxypropyl)indazolinone (9N) and Nl- ethyloxycarbonyl-O-allyl-5-(3- hydroxypropyl)indazolinone (90) Synthesis of allylbenzyl ether (1) (See Andrew et al. , Tetrahedron, 1997,53:13063). To a suspension of sodium hydride (10.2 g, 254 mmol, 1.1 eq. ) in dry THF (250 mL) was added via cannula a solution of benzyl alcohol (25.0 g, 231 mmol, 1.0 eq. ) in dry THF (50 mL). The reaction was stirred at room temperature for two hours under an inert atmosphere. Allyl bromide (23.0 mL, 254 mmol, 1.1 eq. ) was then added dropwise. The resulting suspension was stirred overnight at room temperature. The solvent was partially removed in vacuo and saturated ammonium chloride solution (100 mL) was added. The aqueous phase was extracted with ethyl acetate (3 x 150 mL) and the combined organic extracts were dried (MgS04) and concentrated in vacuo. The crude oil was purified by flash chromatography eluting with 5% ethyl acetate/hexane to give the desired product (1) as a colourless oil (34.0 g, 229 mmol, 99%). ?H NMR 8 7.39-7.27 (m, 5 H; Ar-H), 5.98 (ddt, J = 17.3,10.4, 5.6 Hz, 1 H; CH=CH2), 5.33 (ddt, J = 17.3, 1.6, 1.6 Hz, 1 H: CH=CHtrans), 5.22 (ddt, J = 10.4,1.4, 1.4 Hz, 1 H: CH=CHcis), 4.54 (s, 2 H; OCH2Ph), 4.05 (ddd, J = 5.6,1.4, 1.4 Hz, 2 H; OCH2CH) Synthesis of methyl 2-amino-5-[3- enzyloxy)propyl]benzoate (3) and 2-amino-5-[3- (benzyloxy)propyl]benzoic acid (4) (one-pot procedure) Solid 9-BBN dimer (4.38 g, 35.9 mmol, 1.65 eq. ) was transferred to a 500 mL 3-neck flask fitted with a condenser’under an inert atmosphere. Freshly distilled dry THF (220 mL) and allylbenzyl ether (1) (5.60 g, 37.8 mmol, 1.74 eq. ) were added. The reaction mixture was then stirred for 3 hours at room temperature. The final concentration of the allyl benzyl ether in THF is 0.16M, (see Tallarico et al. , J. Comb. Chem. , 2001,3:312) which is the appropriate concentration for the subsequent Suzuki coupling. To the resulting alkylborane-containing THF solution was added methyl 5-iodoanthranilate (2) (5.00 g, 21.7 mmol, 1.0 eq.), tetrakis(triphenylphosphine)palladium(0) (627 mg, 2.50% mol) and NaOH solution (2.0 M, 21.7 mL, 2.0 eq. ). The reaction was then refluxed for 24 hours. The presence of 9-BBN by-products made the purification of (3) difficult; for purpose of characterisation, (3) was purified from an aliquot of the reaction by flash chromatography eluting with 20% ethyl acetate/hexane and analysed as follows : ?H NMR 8 7.59 (d, J = 2.2 Hz, 1 H; Ar-H), 7.26-7.14 (m, 5 H; Ar-H), 6.99 (dd, J = 8.4,2.1 Hz, 1 H; Ar- H), 6.48 (d, = 8.4 Hz, 1H: Ar-H), 4.40 (s, 2 H; OCH2Ph), 3.75 (s, 3 H; OCH3) , 3.37 (t, J = 6.3 Hz, 2 H; OCH2CH2), 2.51 (m, 2 H) ; ArCH2CH2) , 1.79 (m, 2 H; CH2CH2Ar) ; ??C NMR # 168.5,148.5, 138.5,134.5, 130.3, 129.5, 128.2,127.5, 127.4,116.8, 110.5, 72.8,69.3, 51.3,31.3, 31.1; HMQC , HBMC are consistent with the proposed structure (3) ; LRMS (CI+)m/z: 300 [M+H]+, HRMS (CI+) calculated for C18H22NO3 [M+H]+:300.1600, found: 300.1595. A solution of aqueous sodium hydroxide (2.0M, 20 mL) was added to the crude reaction mixture and the biphasic solution refluxed for 5 days. The mixture was then cooled, filtered through celite, neutralised with diluted aqueous hydrochloric acid solution to pH 7, and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The resulting oil was extracted with hot petroleum ether 40-60 (5 x 200 mL) and on cooling the desired product (4) was obtained as an off white solid (3.50 g, 12.3 mmol, 60%). ?H NMR 8 7.74 (d, J = 2.3 Hz, 1 H), 7.36-7.25 (m, 5 H; Ar-H), 7.16 (dd, J = 8.5,2.3 Hz, 1H; Ar-H), 6.64 (d, J = 8.5 Hz, 1 H; Ar-H), 4.51 (s, 2 H; OCH2Ph) , 3.48 (t, J = 6.4 Hz, 2 H; OCH2CH2) 2.62 (m, 2 H; ArCH2CH2), 1.89 (m, 2 H, ArCH2CH2) ; ??C NMR 8 162.6, 144.5,138.4, 134.5,132.3, 128.3,127.6, 127.5, 121.2,115.8, 111.6,72.8, 69.3,31.9, 31.4 HMBC, HMQC are consistent with the proposed structure (4); LRMS (ES-) m/z: 284 [M-H]+; HRMS calculated for C17H18N03 [M-H]+. 284.1287, found 284.1279. Synthesis of 2-iodo-5-[3-(benzyloxy)propyl]benzoic acid (5) A solution of sodium nitrite (125 mg, 1.77 mmol, 1.03 eq.) in water/acetonitrile (1: 1, 5.0 mL) was added with continuous stirring to a solution of (4) (500 mg, 1.75 mmol, 1.0 eq. ) in aqueous hydrochloric acid solution (13%, v/v) at such a rate that the reaction temperature remained below 5C. After addition was complete, the solution was stirred for 15 minutes and potassium iodide (454 mg, 2.74 mmol, 1.56 eq. ) in aqueous sulphuric acid solution (10%, v/v, 5 mL) was added. The reaction was then heated for 10 minutes at reflux and cooled to room temperature. Saturated sodium thiosulphate solution (5 mL) was added and the reaction was extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The crude oil was purified by flash chromatography eluting with 20 to 100% ethyl acetate/hexane t…

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-5-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; WO2005/121096; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 77317-55-6,Some common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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.

Example 2: Synthesis of methyl 5-iodo-2-(nitro amino) benzoatewherein X is I and R is Me. One hundred g of methyl 2-amino-5-iodobenzoate was dissolved in 1000 ml of acetic acid. Then 100 ml of fuming nitric acid was added to the reaction solution at 150C slowly so that the internal temperature did not exceed 2O0C. The reaction solution was stirred for 30 minutes. Afterwards, 110 ml of acetic anhydride was added to the reaction solution at 2O0C or less, followed by stirring for 1 hour. Then the reaction solution was poured into 2 L of ice water, stirred for 30 minutes, and filtered to obtain 104 g (yield: 90%) of the compound of interest which is in a yellowish solid: 1H NMR (300 MHz, DMSO), delta 8.19 (d, IH, J=2Lambda Hz), 8.07 (dd, IH ,J=8.7, 2.1 Hz), 7.21 (d, IH, J=8.7 Hz), 3.80 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-iodobenzoate, its application will become more common.

Reference:
Patent; PHARMACOSTECH CO., LTD.; KIM, Jae Won; CHA, Young Gwan; RYU, Hyung Chul; KIM, Sun Joo; KIM, Sang Hyun; JEON, Tae Hong; WO2010/67912; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 77317-55-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3, Preparation of Methyl 2-(acetoacetylamino)-5-iodobenzoate.; A solution of methyl 2-amino-5-iodobenzoate (17.9 g, 64.6 mmol) and methylacetoacetate (7.0 mL, 64.6 mmol) in toluene (250 mL) was heated to reflux using a Soxhlet extractor filled with 3 angstrom molecular sieves. After 24 h, the molecular sieves were replaced, more methylacetoacetate (3.75 mL, 32.3 mmol) was added, and the solution was refluxed 2 days. Concentration in vacuo and wash with diethyl ether afforded 24.7 g (76%) of methyl 2-(acetoacetylamino)-5-iodobenzoate as an off-white powder. LCMS: Rt = 1.70 min, [MH+362.0].

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/118583; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 77317-55-6, The chemical industry reduces the impact on the environment during synthesis 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, I believe this compound will play a more active role in future production and life.

To a solution of methyl 5-iodoanthranilate (1.5 g, 5.3 mmol) and sodium bicarbonate (892 mg, 10.6 mmol) in DCM (29.5 mL) at 0 C. was added methyl 3-chloro-3-oxopropionate (587 muL, 5.3 mmol) dropwise over 2 minutes. The cream-colored mixture was stirred at 0 C. for 19 hours. The reaction mixture was then diluted with DCM (25 mL), water (25 mL) was added and the biphasic mixture stirred vigorously for 15 minutes. The layers were separated and the aqueous extracted with DCM (25 mL). The organics were combined, dried (Na2SO4), filtered and concentrated to dryness to afford a cream-colored solid. The crude material was purified by FCC (0-50% EtOAc/hexanes) to provide the title compound as a cream-colored solid.

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 77317-55-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an argon atmosphere 200 mg (0.72 mmol) 2-amino-5-iodo-benzoic acid methyl ester is dissolved in 4.0 ml toluene, 156 mg (0.94 mmol) 2-ethoxy-phenylboronic acid, a solution of 475 mg (2.17 mmol) tripotassium phosphate in 0.5 ml water, 53 mg (0.06 mmol) Pd2(dba)3, and 28 mg (0.10 mmol) N-phenyl-2-di-tert.-butylphosphinopyrrole are added. The reaction mixture is heated to 100 C. and stirred over night. After cooling to room temperature the reaction mixture is filterd over celite and the filtrate is evaporated under reduced pressure. The residue is purified by preparative HPLC (eluent A: water+0.13% TFA, eluent B: acetonitrile). The product is dissolved in dichloromethane and extracted with a saturated aqueous solution of Na2CO3. The organic layer is dried and evaporated under reduced pressure. yield: 40 mgRT (Microsorb 1s)=1.72 minESI-MS (M-FH)+=272

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/249158; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 94 2-Amino-5-iodobenzyl alcohol STR205 A solution of diisobutylaluminium hydride (210 cm3 of a 1.5M solution in THF) was added at -30 to a stirred solution of methyl-2-amino-5-iodobenzoate (28.0 g) in THF (100 cm3) under nitrogen. The mixture was warmed to room temperature, stirred for 16 hours and treated with methanol (35 cm3). Ethyl acetate (500 cm3) was added and the mixture filtered to remove inorganic material. The filtrate was concentrated in vacuo to afford a solid which was chromatographed on silica (Merck “MK 60.9385”) eluding wiht chloroform:methanol, 49:1 (by volume), and the requisite fractions were combined and evaporated in vacuo to give 2-amino-5-iodobenzyl alcohol, m.p. 125, (19.0 g). Analysis %: Found: C, 34.4; H, 3.2; N, 6.0; Calculated for C17 H8 INO: C, 33.8; H, 3.2; N, 5.6.

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; Pfizer Inc.; US4710507; (1987); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com