Methanol → 3-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-one

HRID 620589Notes

Reaction equation

HRID 620589 reaction equation
CO.[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7][C:6](=[N:21]O)[C:5]1=[O:23]>[Ni]>[NH2:21][CH:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH3:3])[C:5]1=[O:23]

Participants

4

Reactant 2

HCID 887MethanolHCID 42938991H-1,4-Benzodiazepine-2,3-dione, 1-methyl-5-phenyl-, 3-oxime

Product 1

HCID 27296813-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 150 ml of methanol containing 5 g (17.9 mmole) of 1,3-dihydro-1-methyl-3-oximino-5-phenyl-1,4-benzodiazepin-2-one was treated with a slurry of active Raney-nickel catalyst1 (10 g wet weight). The resulting suspension was hydrogenated on a Parr apparatus at 60 psi and 23° C. for 30 hours. The catalyst was removed by filtration and the filtrate was concentrated to afford the title compound in 95% yield.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-69e5d91a75734a1cbbe1d1ff506b9cbd
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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