1,1'-Carbonyldiimidazole → 3-Methyl-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

HRID 2235563Notes

Reaction equation

HRID 2235563 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[NH2:9].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C1COCC1>[CH3:1][N:2]1[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[NH:9][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12239324N3-Methylpyridine-3,4-diamine

Product 1

HCID 122993553-Methyl-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-oneYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.80 g (22.7 mmol) of N3-methylpyridine-3,4-diamine in 125 mL of THF was added 4.42 g (27.3 mmol) of 1,1′-carbonyldiimidazole and the reaction was stirred overnight at room temperature. The reaction slurry was concentrated in vacuo to a volume of about 65 mL and cooled in a −10° C. bath, filtered, and the solids washed with 25 mL of THF. The solids were dried under high vacuum to give 2.35 g (69%) of the title compound.

Workup

  1. concentrationThe reaction slurry was concentrated in vacuo to a volume of about 65 mL
  2. temperaturecooled in a −10° C. bath
  3. filtrationfiltered
  4. washthe solids washed with 25 mL of THF
  5. customThe solids were dried under high vacuum

Sources & evidence

ORD record
ord-8937800d1d764760a2ea1616198cf202
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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