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 1687060Notes

Reaction equation

HRID 1687060 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-a148cefbf8214e83ba5bc9acc4d346ee
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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