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 5580Notes

Reaction equation

HRID 5580 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.[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 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In ethanol (500 ml) is dispersed 10% Pd-C (5 g), and thereto is added 5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (64.1 g), and the mixture is subjected to catalytic reduction at ordinary room temperature under atmospheric pressure. After reduction, 10% Pd-C is removed by filtration, and the filtrate is concentrated under reduced pressure to give 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (56.1 g) as white powder, mp. 120°-122° C.

Workup

  1. customis subjected to catalytic reduction at ordinary room temperature under atmospheric pressure
  2. customAfter reduction, 10% Pd-C is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5863f8a43c894049b8ad42ad0415ff02
Source dataset
uspto-grants-1993_09
Patent number
US05244898

Reaction notes

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