Water → 1,2-Dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-pyridine

HRID 579959Notes

Reaction equation

HRID 579959 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5](C#N)=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1.O.O.N>P(=O)(O)(O)O>[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4593OlprinoneHCID 12896473Azane;hydrate

Product 1

HCID 138523301,2-Dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

In 10 ml of 85% phosphoric acid was refluxed 1 g of 1,2-dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-3-pyridinecarbonitrile for 18 hours. After cooling, water was added and then conc. ammonia water was further added to the reaction mixture to render the mixture alkaline. The mixture was extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was removed by distillation under reduced pressure. The residue was recrystallized from ethanol-ether to obtain 0.4 g of 1,2-dihydro-6-methyl-5-(imidazo[1,2-a]pyridin-6-yl)-2-oxo-pyridine.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with chloroform
  3. washAfter washing with water
  4. dry with materialdrying over magnesium sulfate, chloroform
  5. customwas removed by distillation under reduced pressure
  6. customThe residue was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-433b9ba5f003462186bbd80d1cbc6c02
Source dataset
uspto-grants-1988_06
Patent number
US04751227

Reaction notes

Loading…