Bromoacetic Acid → HCID 66747421, compound
Reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]>>[CH3:6][O:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([NH:16][CH2:2][C:3]([OH:5])=[O:4])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]Participants
3
Conditions
- Temperature
- 58 °C
Procedure
Bromoacetic acid (0.876 g, 6.31 mmol, 0.5 eq) is added portionwise to 3,4-dimethoxy-2-nitro-phenylamine (2.5 g, 12.61 mmol, 1.0 eq) and the mixture is stirred at 58° C. for 16 hours. The reaction is then quenched by 25% ammonia in water and diluted with water. The solid is filtered off and washed with 10% ammonia in water. The combined solutions are acidified by concentrated hydrochloric acid and the resulting precipitate is collected by filtration, washed with water and dried under vacuum to afford (3,4-dimethoxy-2-nitro-phenylamino)-acetic acid as a red solid (1.1 g, 34% yield).