6-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one → HCID 57853793, compound

HRID 1040652Notes

Reaction equation

HRID 1040652 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:14])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.COC1C2CCCC(=O)NC=2C=CC=1[N+:29]([O-:31])=[O:30]>>[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:14])[NH:8][C:7]=2[C:6]([N+:29]([O-:31])=[O:30])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 99423616-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneHCID 57853800HCID 57853800, compound

Product 1

HCID 57853793HCID 57853793, compound

Procedure

Analogous to procedure 107b, 6-Methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (700 mg, 3.66 mmol) was converted to 6-Methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (380 mg, 44%), purified by ISCO chromatography. 1H-NMR (CDCl3) δ 8.12 (s, 1H), 7.79 (d, J=8.6 Hz, 1H). 6.85 (d, J=8.6 Hz, 1H), 3.95 (s, 3H), 2.95 (t, J=7.2 Hz, 2H), 2.44 (t, J=7.3 Hz, 2H), 2.31 (quint, J=7.2 Hz, 2H); LC/MS (ESI-pos) m/z 237.11 (M+H). Analogously, 6-Methoxy-9-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one was also isolated.

Workup

  1. custompurified by ISCO chromatography

Sources & evidence

ORD record
ord-105c89a640d1489e8d1bba3b0f1d21b9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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