Ammonia → 2(1-Iminoethyl)-4-nitrophenol

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])=O.[NH3:14].CO>>[NH:14]=[C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])[CH3:1]

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 2480792'-Hydroxy-5'-nitroacetophenone

Product 1

HCID 1370147772(1-Iminoethyl)-4-nitrophenolYield 100%

Procedure

A mixture of 2-hydroxy-5-nitroacetophenone (2.96 g, 16.34 mmol) and ammonia in MeOH (11.67 mL, 82 mmol) was stirred for 1 hr at rt. The reaction mixture was concentrated to afford the crude title product (2.94 g, 16.32 mmol, 100% yield) as a yellow solid. tR: 0.53 min (LC-MS 2); ESI-MS: 181 [M+H]+ (LC-MS 2).