1-Tetralone → 3-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one
Reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH2:4][CH2:3]1.BrC1C(=O)NC2C=CC=CC=2CC1.C1(=O)C2C(=CC=CC=2)CCC1.[N-:38]=[N+:39]=[N-].[Na+]>>[N:1]([CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH2:4][CH2:3]1)=[N+:38]=[N-:39]Participants
5
Procedure
In U.S. Pat. No. 4,873,235, W. H. Parsons et al. describes the synthesis of 3-amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one by reacting 3-bromo-1,3,4,5-tetrahydro-benzo[b]azepin-2-one, which is synthesized by bromination of 1-tetralone, followed by reaction with sodium azide to form 3-azido-1,3,4,5-tetrahydro-benzo[b]azepin-2-one. Subsequent hydrogenation of the azido group e.g. by reaction with sodium cyanoborohydride or in the presence of hydrogen on a suitable catalyst leads to 3-amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one.
Sources & evidence
- ORD record
- ord-90aae1c4d4de45a08f04c3e923b7e0e6
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166720B2
Reaction notes
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