Category: 35944-64-0

Some common heterocyclic compound, 35944-64-0, name is 3-Iodo-4-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. Product Details of 35944-64-0

3-Iodo-4-methylphenol (1-1), A mixture of 8 mL of concentrated H2SO4, 12 mL of water, 3-iodo-4-methylanine (5.00 g, 21.5 mmol) and 20 g of ice was stirred under ice-bath cooling until a paste resulted. To this paste was added slowly an ice-cold solution OfNaNO2 (1.55 g, 22.4 mmol) in 3.5 niL of water and the resulting mixture stirred for 20 minutes while maintaining the temperature at < 5 C. The resulting suspension was slowly added to a mixture of 26 mL of concentrated H2SO4 and 24 mL of water preheated to 80 C. This mixture was stirred at 80 C for 15 min, then chilled in an ice-bath and poured onto 200 g of ice. The resulting mixture was extracted with 100 mL of EtOAc, and the organic extract washed with water, brine, dried (MgSO4) and evaporated to give a residue. The residue was adsorbed onto 15 g of Sitheta2&om CH2Cl2, loaded into a precolumn and subjected to MPLC through a 120 g column Of SiO2 eluting with 5% EtOAc in hexanes (10 min) and then 10% EtOAc (20 min) to provide 3- iodo-4-methylphenol 1-1 as an oil 1H NMR (300 MHz, DMSO-d6): delta 2.25 (s, 3H), 6.71 (dd, IH5 J= 8, 2 Hz), 7.11 (d, IH, J- 8 Hz), 7.23 (d, IH, J= 2 Hz), 9.51 (s, IH); LC-MS: calculated for C7H7IO 234.0 observed m/e 234.6 (M + H)+. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35944-64-0, its application will become more common. Reference:
Patent; MERCK SHARP &amp; DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 35944-64-0, name is 3-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 35944-64-0

4-(4-methylpiperazin-1-yl-methyl)-3-trifluoromethyl-benzoic acid (0.755 g, 2.5 mmol, 1.0 eq), HATU (O-(7-azabenzotriazol-1-oxo)-N, N, N?, N?-tetramethyluronium hexafluorophosphate) (1.14 g, 3 mmol, 1.2 eq), DIPEA (1.29 g, 10 mmol, 4.0 eq) was dissolved in methylene chloride. The mixture was stirred at room temperature for 0.5 h and to the solution 3-iodo-4-methylaniline (582.6 mg, 2.5 mmol, 1.0 eq) was added. Then the mixture was stirred at 45 C. overnight, evaporated to dryness after the completion of the reaction, extracted with saturated aqueous sodium bicarbonate and methylene chloride 3 times. The organic layer was combined and concentrated under reduced pressure. The residue obtained was isolated by column chromatography to give the title product as a light yellow solid (892 mg, 69.0% yield). 1H NMR (400 MHz, CDCl3) 8.10 (s, 1H), 8.08 (d, J=2 Hz, 1H), 8.08-8.05 (m, 1H), 8.0 (s, 1H), 7.95 (s, 1H), 7.55 (dd, J=4, 2 Hz, 1H), 7.20 (d, J=8 Hz, 1H), 3.75 (s, 2H) 2.60-2.41 (m, 8H), 2.40 (s, 3H), 2.30 (s, 3H). MS m/z (ESI): 518.1 [M+H].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 35944-64-0.

Reference:
Patent; Si Chuan University; Yang, Shengyong; Wei, Yuquan; (168 pag.)US2017/305920; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 35944-64-0, name is 3-Iodo-4-methylaniline, 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 35944-64-0. 35944-64-0

2/6-Difluoro-N-(2′-methyl-5I-(pyridin-2-ylmethoxy)biphenyl-4-yl)benza?iotaide[00150] To a solution of 3-iodo-4-methylaniline (1 g, 4.29 mmol) in H2O (25 mL) was added H2SO4 (0.5 M, 25 mL). The solution was heated to 8O0C until all solid dissolved. Then the reaction was cooled to 00C, and NaNCh (0.44 g, 6.39 mmol) was added in small portions. After 2 hr at this temperature, urea (0.13 g, 2.1 mmol) was added at 00C. The solution was allowed to warm up to room temperature, and H2SO4 (0.5 M, 25 mL) was added. The reaction was refluxed for 30 min and cooled down to room temperature. The solution was extracted with EtOAc and EbO, and the combined organic phases were dried over Na2SO4, concentrated, and chromatographied to give the pure product 1 (0.8 g, 80%). Following the general Suzuki coupling procedure, 2 was prepared.[00151] The solution of 2 (0.4 g, 1.18 mmol), 2-picolyl chloride hydrochloride (0.215 g, 1.31 mmol), and K2CO3 (0.325 g, 2.35 mmol) in DMF (5 mL) was heated at 500C for 48 hr. The reaction solution was diluted with H2O (15 mL) and extracted with EtOAc (25 mL). Column chromatography (Hexanes/EtOAc=l/l) afforded Compound 4 in 56% yield.[00152] 1H NMR (400 MHz, CDCl3) delta 8.59 (d, / = 4.8 Hz, 1 H), 7.74-7.66 (m, 4 H), 7.55-7.52 (m, 1 H), 7.48-7.40 (m, 1 H), 7.34-7.32 (m, 2 H), 7.24-7.16 (m, 2 H), 7.02 (t, / = 8.0 Hz, 2 H), 6.90-6.87 (m, 2 H), 5.21 (s, 2 H), 2.21 (s, 3 H); ESMS cacld (C26H20F2N2O2): 430.1; found: 431.1 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Iodo-4-methylaniline.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; JIANG, Jun; ZHANG, Junyi; CHEN, Shoujun; SUN, Lijun; WO2010/39238; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 35944-64-0, name is 3-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., 35944-64-0

Adapting literature procedures (Jian, et al., U.S. Application Publication No. 2006/173006 and International Application Publication No. WO 2010/039238; Bookster, et al., International Application Publication No. WO 2010/047982), to a solution of commercial 3-iodo-4-methylaniline (1.0 g, 4.30 mmol) in water (25 mL) was added aqueous 0.5 M sulfuric acid (H2SO4) (25 mL, 12.5 mmol). The reaction mixture was heated at ~80C (oil bath) until all solids were dissolved to yield a pale brownish solution. The solution was cooled quickly to ~0C (ice bath) upon which part of 3-iodo-4-methylaniline began to precipitated as crystals. To the reaction mixture was added in small portions solid sodium nitrite (NaN02) (444 mg, 6.39 mmol). After ~2 hours at ~0 C (ice bath), the reaction mixture became a clear yellow solution. Urea (H2NCONH2) (126 mg, 2.1 mmol) was added at this temperature and the solution was allowed to warm gradually to room temperature. Aqueous 0.5 M sulfuric acid (H2SO4) (25 mL, 12.5 mmol) was added and the reaction mixture was heated at reflux for -30 min followed by cooling to room temperature. Extractive aqueous work-up with ethyl acetate and purification bysilica gel column chromatography using an EtOAc/hexane mixture (EtOAc/hexane = 1 :8, v/v) provided the target compound as a deep orange oil. Rf. -0.37 (EtOAc/hexane = 1 :9, v/v). 1H MR (400 MHz, CDC13): delta 7.30 (d, J = 2.0 Hz, 1H), 7.06 (d, J= 8.4 Hz, 1H), 6.72 (dd, J= 8.4, 2.4 Hz, 1H), 4.71 (br. s, 1H) ppm. The analytical data correspond to the data for the compound in the literature. 3-Iodo-4-methyl phenol (l-methyl-2-iodo-4-hydroxybenzene) is also commercially available.

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Reference:
Patent; QUADRIGA BIOSCIENCES, INC.; JANDELEIT, Bernd; FISCHER, Wolf-Nicolas; KOLLER, Kerry J.; RINGOLD, Gordon; (469 pag.)WO2017/24009; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com