Ammonia → 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol
Reaction equation
N([O-])=[O:2].[Na+].[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21](N)[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N>S(=O)(=O)(O)O.O>[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([OH:2])[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
Sodium nitrite (609 mg) aqueous solution (6 ml) was added dropwise to a stirred suspension of N7 -benzyl-6,7-dihydro-5H-benzocycloheptene-2,7-diamine (2.22 g) in 6N sulfuric acid (22 ml) under ice cooling over 15 minutes and the resulting solution was stirred at the same temperature for 30 minutes. The solution was added dropwise to a stirred solution of sulfuric acid (3 ml) in water (15 ml) at 75° C. over 15 minutes. The resulting mixture was stirred at the same temperature for 30 minutes, cooled with ice-water bath, basified with 28% ammonia solution (15 ml), and extracted six times with dichloromethane. The combined extracts were evaporated in vacuo and chromatographed over silica gel using dichloromethane and methanol to afford 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol (1.72 g) as a pale brown oil.
Workup
- stirringThe resulting mixture was stirred at the same temperature for 30 minutes
- temperaturecooled with ice-water bath
- extractionextracted six times with dichloromethane
- customThe combined extracts were evaporated in vacuo
- customchromatographed over silica gel
Sources & evidence
- ORD record
- ord-1fab16b4d4b0485c9c3a08db36b3902e
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387710
Reaction notes
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