3-methyl-4-nitro-1H-imidazo[4,5-c]pyridin-2(3H)-one → 4-Amino-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

HRID 2235565Notes

Reaction equation

HRID 2235565 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([N+:11]([O-])=O)=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:14]>CO.[Ni]>[NH2:11][C:7]1[C:6]2[N:2]([CH3:1])[C:3](=[O:14])[NH:4][C:5]=2[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 124290963-methyl-4-nitro-1H-imidazo[4,5-c]pyridin-2(3H)-one

Product 1

HCID 135163734-Amino-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a nitrogen inerted slurry of 2.24 g (11.5 mmol) of 3-methyl-4-nitro-1,3-dihydroimidazo[4,5-c]pyridin-2-one in 25 mL of methanol was added 0.5 mL of Raney nickel (50% slurry in water). The reaction slurry was purged with hydrogen and then stirred under balloon pressure hydrogen for 1 h. To the reaction slurry was added 20 mL of methanol and the reaction slurry was purged with hydrogen and then stirred under balloon pressure hydrogen for 2 h.

Workup

  1. customThe reaction slurry was purged with hydrogen
  2. additionTo the reaction slurry was added 20 mL of methanol
  3. customthe reaction slurry was purged with hydrogen
  4. stirringstirred under balloon pressure hydrogen for 2 h.

Sources & evidence

ORD record
ord-2281a50c8673440ab5d55270c0abedf3
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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