Hydrochloric Acid → N-(4-nitrophenyl)pentanamide

Reaction equation

[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[N+:8]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O-:10])=[O:9].Cl>N1C=CC=CC=1>[N+:8]([C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

Procedure

Valeryl chloride (12.06 g., 0.10 mole) is added dropwise to a cooled stirred solution of 4-nitroaniline (13.81 g., 0.10 mole) in pyridine (100 ml.). The resulting mixture is stirred at ambient temperature for one hour then heated (80°-100° C.) for twenty-four hours. The cooled solution is poured into cold 1 N hydrochloric acid (500 ml.) with stirring. The precipitated solid is collected, washed with water and dried, 21.4 g., m.p. 107°-116° C. Recrystallization from butyl chloride provides material of m.p. 115°-118° C.