Nitric Acid → 2-Acetylamino-4-chloro-5-nitrobenzoic acid methyl ester
Reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:23])[CH3:22]>>[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[C:17]([N+:6]([O-:9])=[O:7])[C:16]([Cl:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:23])[CH3:22]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3 mL conc. sulfuric acid and 0.40 mL of 90% nitric acid at 0° C. was added 2-acetylamino-4-chlorobenzoic acid methyl ester (1.5 g) in three portions over a period of 20 minutes. This was stirred at 0° C. for 30 minutes then allowed to warm to room temperature for an additional 1 hour. At this time the reaction was poured into 50 mL of an ice/water mixture and extracted with ethyl acetate (3×50 mL). The combined organics were washed sequentially with water (2×50 mL), 10% sodium bicarbonate (2×50 mL) and brine (50 mL) then dried over magnesium sulfate and concentrated in vacuo. Recrystallization of the crude product from methanol gave the title compound (1.02 g).