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

HRID 2235564Notes

Reaction equation

HRID 2235564 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:11].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:6]2[C:7]([N+:12]([O-:14])=[O:13])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 122993553-Methyl-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

Product 1

HCID 124290963-methyl-4-nitro-1H-imidazo[4,5-c]pyridin-2(3H)-oneYield 86.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 1.73 g (11.6 mmol) of 3-methyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one in 6.3 mL of concentrated sulfuric acid, cooled in an 0° C. ice bath, was slowly added a solution of 1.50 mL (36.0 mmol) of fuming nitric acid in 1.5 mL of concentrated sulfuric acid. The reaction was removed from the ice bath and stirred for 0.5 h at room temperature and then heated at 100° C. for 2 h. The reaction was quenched over 300 mL of ice and solid ammonium carbonate was added to adjust the pH to 9. The resulting slurry was filtered and the collected solids washed with water and dried under high vacuum to give 1.94 g (86%) of the title compound.

Workup

  1. customThe reaction was removed from the ice bath
  2. temperatureheated at 100° C. for 2 h
  3. customThe reaction was quenched over 300 mL of ice and solid ammonium carbonate
  4. additionwas added
  5. filtrationThe resulting slurry was filtered
  6. washthe collected solids washed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-0170544f77304138add9b446a6324761
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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