8-Methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one → 7-Amino-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

HRID 1687061Notes

Reaction equation

HRID 1687061 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-])=O)=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C:9](=[O:13])[CH2:8][C:7]=2[CH:14]=1>CO.[Pd]>[NH2:15][C:4]1[C:3]([O:2][CH3:1])=[CH:14][C:7]2[CH2:8][C:9](=[O:13])[NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 135206918-Methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

Product 1

HCID 672632937-Amino-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-oneYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (360 mg, 1.5 mmol) in methanol (30 mL) was added palladium 10% wt on Carbon (50% wet; 50 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) for 30 minutes. Filtration through Celite and evaporation of the solvent provided 7-amino-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (300 mg, 95%) as a tan solid. 1H-NMR (CDCl3) δ 6.54 (s, 1H), 6.47 (s, 1H), 5.80 (br s, 1H), 3.82 (s, 3H), 3.73 (s, 2H), 3.71 (br s, 2H), 3.53 (q, J=6.3 Hz, 2H), 2.96 (t, J=6.1 Hz, 2H); LC/MS (ESI+): 207.13 (M+H).

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent

Sources & evidence

ORD record
ord-b6427dcde56b497d90f0e0d89410b683
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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