Formic Acid → Imidazo(1,5-a)pyridine

HRID 66022Notes

Reaction equation

HRID 66022 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH:9](O)=[O:10]>>[CH:2]1[N:1]=[CH:9][N:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=12.[CH:9]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 195092-Pyridinemethanamine

Product 2

HCID 274090Imidazo(1,5-a)pyridineHCID 12228441N-Pyridin-2-ylmethyl-formamide

Procedure

A mixture of 32.4 g. of 2-aminomethylpyridine and 96 ml. of 97% formic acid is heated under reflux for 3.5 hrs. The resulting solution is subjected to vacuum distillation, the desired product, 2-formamidomethylpyridine, being isolated as a yellow oil crystallizes to a solid having a melting point at about room temperature.

Workup

  1. additionA mixture of 32.4 g
  2. temperatureunder reflux for 3.5 hrs
  3. distillationThe resulting solution is subjected to vacuum distillation

Sources & evidence

ORD record
ord-5ca0481216164114858a8a1f1139e1bb
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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