Pyridine → 8-Acetoxy-2-methylimidazo[1,2-a]pyridine

HRID 613617

Reaction equation

HRID 613617 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].N1C=CC=CC=1>ClCCl>[C:12]([O:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8209532-Methylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 183219268-Acetoxy-2-methylimidazo[1,2-a]pyridineYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (10 g), acetic anhydride (10.3 g) and pyridine (10.7 g) in anhydrous dichloromethane (100 ml) was stirred for 1 hour at ambient temperature and allowed to stand overnight. The 30 mixture was washed with water, and the organic layer was separated. The aqueous layer was neutralized with sodium bicarbonate and extracted with chloroform. The combined organic layers were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo to give 8-acetoxy-2-methylimidazo[1,2-a]pyridine (13.1 g) as oil.

Workup

  1. waitto stand overnight
  2. washThe 30 mixture was washed with water
  3. customthe organic layer was separated
  4. extractionextracted with chloroform
  5. washThe combined organic layers were washed with saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c73c14e2cff948938980e69f1e0397eb
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Linked notes

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