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

HRID 1871117Notes

Reaction equation

HRID 1871117 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 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 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-69a2ebb23ad44ffa936ebd1b1424c79f
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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