Ammonia → 8-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepine

Reaction equation

[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[N+:12]([O-])([O-:14])=[O:13].[K+].N>OS(O)(=O)=O>[N+:12]([C:10]1[CH:9]=[CH:8][C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][NH:1][C:2]=2[CH:11]=1)([O-:14])=[O:13]

Participants

Procedure

At −10° C., 2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.9 g, 13 mmol) was added dropwise to a solution of KNO3 (3 g, 30 mmol) in H2SO4 (50 mL). The mixture was stirred for 40 min, poured over crushed ice, basified with aq. ammonia to pH 13, and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated to give 8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine as a black solid (1.3 g, 51%), which was used without further purification.