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

HRID 1381668Notes

Reaction equation

HRID 1381668 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 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-15e3b0aaf28e4eb2a736b7b8eb876d68
Source dataset
uspto-grants-1989_02
Patent number
US04803276

Reaction notes

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