4-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one → 1-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

HRID 2203114Notes

Reaction equation

HRID 2203114 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:22]=[C:21]([CH3:23])[N:20]([CH3:24])[C:19]=3[CH:25]=2)[C:11](=[O:26])[CH:10]=1)C1C=CC=CC=1>[Pd].CO>[CH3:24][N:20]1[C:19]2[CH:25]=[C:15]([N:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]3=[O:26])[CH:16]=[CH:17][C:18]=2[N:22]=[C:21]1[CH3:23]

Participants

4

Reactant 1

HCID 896911954-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Product 1

HCID 896909671-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-oneYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (627 mg), 10% Pd/C (193 mg) and MeOH (10 ml) was stirred under H2 atmosphere at room temperature for 1 h. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (421 mg) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-181c4a7519de4a6d814132b0da56589f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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