Category: 771583-12-1

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. 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, A new synthetic method of this compound is introduced below., Quality Control of 2-(Aminomethyl)-4-bromoaniline

In the 1000 ml three-necked bottle,5 g of 5-bromo-2-aminobenzylamine (molecular weight 200, 0.025 mol) was added, Add 150 ml of methylene chloride, stir, dissolve,Add 11 ml of triethylamine and cool to 0 C. Cooling and stirring, A solution of 20 ml of 4.75 g of beta-naphthoyl chloride dissolved in dichloromethane (molecular weight 190,0.025 moles) was slowly added. Natural to room temperature, stirring for 3 hours.Add 40 ml of water, separate the organic phase, evaporated,To obtain a solid intermediate product. The solid was dissolved in 60 ml of toluene,Add 4 ml of thionyl chloride, reflux for three days, cooling, product precipitation,Add 50 ml of concentrated aqueous ammonia, stir, and filter out 8.4 g of solid dihydro compound.The solid dihydro was dissolved in 80 ml of dichloromethane,Adding 2.3 g of manganese dioxide and stirring at room temperature for 18 hours to filter out the inorganic matter,The organic layer was evaporated to dryness and recrystallized to give 5.35 g of 6-bromo-2- (naphthalen-2-yl) quinazoline with a molecular weight of 334 in 64% yield.

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; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Li Yinkui; Shao Shuang; Ren Xueyan; (35 pag.)CN106554319; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 771583-12-1, A common heterocyclic compound, 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, molecular formula is C7H9BrN2, 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.

Step 2: 6-bromo-3.4-dihvdroquinazolin-2(1 H)-one; To a solution of triphosgene (0.445 g, 1.5 mmol) in tetrahydrofuran (20 mL) was added triethylamine (0.454 g, 4.5 mmol) dropwise at 0 0C under nitrogen. After stirring for 30 min, a solution of 2-(aminomethyl)-4-bromoaniline (0.201 g, 1 mmol) in tetrahydrofuran (10 mL) was added dropwise. The mixture was allowed to stir for 16 h at room temperature. The mixture was diluted with water (15 mL) and the pH of the resultant mixture was adjusted to 8 – 9 by the addition of 1 M aqueous sodium hydroxide. The mixture was extracted three times with ethyl acetate (30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The residue was purified by re- crystallization from a mixture o dichloromethane and diethyl ether to give the title compound (0.13 g, 57.5%) as a yellow solid. 1 H NMR (400MHz, DMSO-Cf6) delta ppm 9.12 (s, 1 H), 7.29 (S, 1 H), 7.27(d, J = 8.4 Hz, 1 H), 6.87 (s, 1 H), 6.70 (d, J = 8.4 Hz, 1 H), 4.28 (s, 2H).

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; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, 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. Quality Control of 2-(Aminomethyl)-4-bromoaniline

To dichloromethane (DCM) (3.5 L), 5-bromo-2-amino-benzylamine (137g, 0.5 mol) and triethylamine (TEA) (250 mL, 1.75 mol) were added at O0C on stirring. Then benzoyl chloride (55 mL, 0.45 mol) in DCM (500 mL) was added on stirring at such a rate to keep the temperature at 0-50C. The mixture was stirred for 3 hours at r.t.. Water (1 L) was added and the organic phase was separated, washed with water and dried. The solvent was evaporated and SOCl2 (100 mL) was added to the residue (147.5 g) suspended in toluene (1.5 L). The obtained suspension was heated at reflux for 72 hours. On cooling a precipitate was formed, it was filtered, washed with toluene and suspended in aqueous ammonia, the suspension was extracted with AcOEt. The combined organic phases were washed with water, dried and concentrated to afford the dihydroquinazoline derivative, as a light brown solid (93.8 g., 64% yield). The dihydroquinazoline was dissolved in DCM (2 L) and MnO2 (56.28 g) was added on stirring. The resulting suspension was stirred at r.t. for 18 hours. The suspension was filtered on celite, the cake was washed with DCM and the combined filtrate and washings were concentrated to afford the titled product as an amorphous solid, 85.54 g (60 % overall yield; 95% oxidation yield). Ci4H9BrN2; MW: 285.15; MS m/z: 286 (M+ 1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, IH), 8.17 (dd, IH), 8.49-8.56(m, 3H), 9.70(s, IH).

The synthetic route of 2-(Aminomethyl)-4-bromoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; WO2009/152868; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary