Sodium Hydroxide → 2-((4-Bromobenzyl)amino)acetamide

Participants

Reaction Steps

To a solution of 4-bromobenzaldehyde (100 g, 0.54 mol) and glycinamide hydrochloride (54 g, 0.48 mol) methanol/water (1500 ml, 5.5/1) was added sodium hydroxide (21.6 g, 0.54 mol). After stirring for 17 h at room temperature the reaction mixture was cooled to 0° C. Sodium borohydride (38 g, 1.0 mol) was added and the mixture was stirred until a clear solution was obtained. The reaction was quenched by addition of concentrated hydrochloric acid until pH=3. After stirring for 17 h the mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate and the product was extracted into dichloromethane. The combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure to afford 2-(4-bromobenzylamino)acetamide (92 g).

Provenance & Evidence