Hydrogen Bromide → HCID 67280330, compound

Participants

Reaction Steps

Cuprous bromide was added in one portion to a hot solution (90° C.) of 2-amino-6-methylbenzoic acid (10 g, 66 mmol) and HBr (26 mL, 40%) in H2O (160 ml). This was followed by the dropwise addition of a solution of NaNO2 (13.7 g, 198 mmol) in H2O (40 ml) over a period of 25 min. The reaction mixture was maintained at same temperature for 1 h and then was heated under reflux for another 0.5 h before it was cooled to room temperature and stirred for 2 h. Upon completion, the reaction mixture was carefully poured into ice water (1000 ml), and 5% NaOH solution was added until a pH of 14 was reached. The resulting suspension was filtered. The filtrate was acidified with diluted HCl to a pH of 1 and extracted with Et2O, Charcoal was added, and the resulting mixture was heated to reflux, filtered and evaporated by a rotatory evaporator to give a crude compound, which was recrystallized from Et2O/PE to afford the product (9.28 g, 65%).

Provenance & Evidence