5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine → 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine

HRID 54745Notes

Reaction equation

HRID 54745 reaction equation
[CH3:1][N:2]([CH3:25])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1>C(O)C.[C].[Pd]>[CH3:1][N:2]([CH3:25])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:24])[C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 107358285-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 107812055-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepineYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5 g of 10% palladium-carbon was dispersed in 500 ml of ethanol. Thereto was added 64.1 g of 5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine. The mixture was subjected to catalytic reduction at normal temperature at normal pressure. After the reduction, 10% palladium-carbon was removed by filtration. The filtrate was concentrated under reduced pressure to obtain 56.1 g of 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. customAfter the reduction, 10% palladium-carbon was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-764ed5681b494484a29002b5e8af4626
Source dataset
uspto-grants-1997_04
Patent number
US05622947

Reaction notes

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