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
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