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

HRID 838939Notes

Reaction equation

HRID 838939 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 hydrioxide 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 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 hydrioxide 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 to a light brown oil, 14.0 g

Sources & evidence

ORD record
ord-e137382566af48a2a59677f4a6bc8d9f
Source dataset
uspto-grants-1978_06
Patent number
US04093616

Reaction notes

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