HCID 12052631, compound → HCID 12052632, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O.[H][H]>O=[Pt]=O.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:6][NH:7][C:8]1[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Procedure

The title compound was prepared by the addition of Adam's catalyst (160 mg, 10% wt.) to a degassed solution of N-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-nitroaniline (1.6 g, 4.69 mmol) in absolute ethanol (25 mL). The atmosphere was replaced with hydrogen then the reaction was stirred vigourously at ambient temperature until all of the nitro compound had been consumed as determined by tlc (9:1 CHCl3:MeOH, 1% TEA). The reaction mixture was filtered through a bed of diatomaceous earth, then the solvent was removed under reduced pressure to give the diamine as a brown yellow oil (1.46 g, 100%).