N-[2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide → N-[2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide

HRID 1687058Notes

Reaction equation

HRID 1687058 reaction equation
[CH3:1][O:2][C:3]1[C:19]([N+:20]([O-])=O)=[CH:18][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH2:10][CH2:11][C:5]=2[CH:4]=1>CO.[Pd]>[NH2:20][C:19]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH2:8][CH2:7][C:6]=2[CH:18]=1

Participants

4

Reactant 1

HCID 67264615N-[2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide

Product 1

HCID 67263716N-[2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamideYield 108.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[2-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide (100 mg, 0.3 mmol) in methanol (20 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 N-[2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide (90 mg, 100%) as a yellow oil, which was used without further purification. 1H-NMR (CDCl3) δ 6.59 (br s, 1H), 6.53 (s, 1H), 6.48 (s, 1H), 3.82 (s, 3H), 3.50-4.40 (br s, 2H), 3.40 (m, 2H), 2.65-2.93 (m, 10H), 2.02 (s, 3H); LC/MS (ESI+): 278.25 (M+H).

Workup

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

Sources & evidence

ORD record
ord-ab1f85ab26d7443fa3d4256235141abb
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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