HCID 57437918, compound → 1,3-dimethyl-7-amino-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reaction equation

[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:16])[CH2:3]1.CC1C2C=C([N+]([O-])=O)C=CC=2CCN(C)C1>[Pd].CO>[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:16])[CH2:3]1

Participants

Procedure

1.4 g (6.3 mmol) of a mixture of 1,3-dimethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine and 1,3-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine, 20 ml of methanol and 0.20 g 10% palladium on charcoal is hydrogenated for 5.5 h under a hydrogen atmosphere (50 psi). It is filtered, concentrated and the mixture is purified by chromatography with silica gel (eluant: dichloromethane:95% ethanol/5% ammonia 99:1 to 80:20). 0.45 g of 1,3-dimethyl-7-amino-2,3,4,5-tetrahydro-1H-benzo[d]azepine are obtained