7-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one → HCID 57853796, compound

HRID 1040591Notes

Reaction equation

HRID 1040591 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[C:6]([N+:15]([O-])=O)=[CH:5][CH:4]=1.NC1C=CC2N(C)C(=O)CCCC=2C=1>>[NH2:15][C:6]1[C:7]2[NH:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][C:13]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 197602587-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-oneHCID 57853793HCID 57853793, compound

Product 1

HCID 57853796HCID 57853796, compound

Procedure

9-Amino-6-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one was prepared from 6-methoxy-9-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one via reduction of the nitro group as described for the preparation of 7-Amino-1-methyl-1,3,4,5-tetrahydrobenzo[b]azepin-2-one. The crude product was purified by flash chromatography (EtOAc) and the product was obtained as a solid (36%); (400 MHz, DMSO-d6) 66.62 (d, J=8.84 Hz, 1H), 6.56 (d, J 8.84 Hz, 1H), 4.52 (br s, 1H), 3.66 (s, 3H), 3.16 (d, J=3.31 Hz, 2H), 2.64 (m, 2H), 2.04 (m, 2H), 1.97 (m, 2H); MS (m/e) 207 (M+H).

Workup

  1. customThe crude product was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-33b0aa4d68f947b2af448b3e6a278aef
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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