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

HRID 1040752Notes

Reaction equation

HRID 1040752 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][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[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][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:8][CH2:7][C:6]=2[CH:18]=1

Participants

4

Reactant 1

HCID 672637882-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide

Product 1

HCID 672635242-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethylacetamideYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide (767 mg, 1.75 mmol) in methanol (30 mL) was added palladium 10% wt on Carbon (50% wet; 100 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 the crude product, which was purified by flash chromatography on SiO2 (MeOH/dichloromethane 0-6%) to give 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide (332 mg, 69%) as a white solid. 1H-NMR (CDCl3) δ 6.54 (s, 1H), 6.48 (s, 1H), 3.81 (s, 3H), 3.53 (br s, 2H), 3.23 (s, 2H), 3.13 (s, 3H), 2.96 (s, 3H), 2.80 (m, 4H), 2.65 (m, 4H); LC/MS (ESI+): 278.67 (M+H).

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent
  3. customprovided the crude product, which
  4. customwas purified by flash chromatography on SiO2 (MeOH/dichloromethane 0-6%)

Sources & evidence

ORD record
ord-3e3ed52647a64c15bbc44e5851887586
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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