(4-Isopropyl-phenyl)-(3-methoxy-2-nitro-phenyl)-methanone → (2-Amino-3-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=2[N+:20]([O-])=O)=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>CO.C1COCC1.[Ni]>[NH2:20][C:13]1[C:14]([O:18][CH3:19])=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1)=[O:11]

Participants

Procedure

A solution of 6.8 g (22 mmol) (4-isopropyl-phenyl)-(3-methoxy-2-nitro-phenyl)-methanone in 90 ml methanol and 40 ml THF is hydrogenated at normal pressure and rt during 20 h in the presence of 2 g Raney nickel. After filtration and evaporation of the solvent the residue is taken up in ether and (4-isopropyl-phenyl)-(3-methoxy-2-nitro-phenyl)-methanone precipitates by the addition of saturated etheric hydrochloric acid as its hydrochloride.