Phosphorus oxychloride → Imidazo(1,5-a)pyridine

HRID 66023Notes

Reaction equation

HRID 66023 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.P(Cl)(Cl)(Cl)=O>>[CH:4]1[N:3]=[CH:1][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12228441N-Pyridin-2-ylmethyl-formamide

Product 1

HCID 274090Imidazo(1,5-a)pyridine

Procedure

To 13.6 g. of 2-formamidomethylpyridine in a round-bottom flask is added 25 ml. of phosphorous oxychloride. Following the exothermic reaction, the reaction mixture is cooled to room temperature, and quenched on crushed ice. The aqueous mixture is treated with sufficient 20% aqueous sodium hydroxide solution to provide a pH of 9-10, and the liberated product extracted into chloroform (3 × 300 ml.). The extracts are combined, dried over sodium sulfate and concentrated to give imidazo[1,5-a]pyridine as a light brown oil, 14.0 g.

Workup

  1. customthe exothermic reaction
  2. customquenched
  3. customon crushed ice
  4. additionThe aqueous mixture is treated with sufficient 20% aqueous sodium hydroxide solution
  5. customto provide a pH of 9-10
  6. extractionthe liberated product extracted into chloroform (3 × 300 ml.)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0fcbfa56acfc45d5b043ecb549bc4a05
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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