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

HRID 838945Notes

Reaction equation

HRID 838945 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 temperture, and quenched on crushed ice. The aqueous mixture is treatedwith 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. temperaturethe reaction mixture is cooled to room temperture
  3. customquenched
  4. customon crushed ice
  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-2fcbae2d6f74460aa95f97dd44d23bc3
Source dataset
uspto-grants-1978_06
Patent number
US04093616

Reaction notes

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