Nitric Acid → n-(3-Chloro-4-nitrophenyl)acetamide
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)(=[O:7])[CH3:6]>O>[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[C:11]([Cl:15])[CH:10]=1)(=[O:7])[CH3:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To fuming nitric acid (120 mL) at -50° C. was added N-acetyl-3-chloroaniline (30 g) over a period of 45 minutes. The reaction was kept between -50° C. and -30° C. using a dry ice/acetone bath. The reaction mixture was stirred for an additional hour and then poured into 1500 mL of crushed ice and water. The precipitate was filtered and slurried with 1 liter of slightly alkaline water (ammonium hydroxide) twice. The precipitate was then dried and recrystallized from toluene to yield (3.6 g) of N-acetyl-3-chloro-4-nitroaniline; m.p. 134°-136° C.