5-(p-Hydroxymethylphenyl)imidazo[1,5-a]pyridine → 5-(p-Formylphenyl)-imidazo[1,5-a]pyridine

HRID 280217Notes

Reaction equation

HRID 280217 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 136494325-(p-Hydroxymethylphenyl)imidazo[1,5-a]pyridine

Product 1

HCID 136494335-(p-Formylphenyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(p-hydroxymethylphenyl)imidazo[1,5-a]pyridine (0.52 g) in 10 ml of methylene chloride is refluxed with 5.2 g of activated manganese dioxide for 24 hours. An additional 5.2 g of manganese dioxide is added and the reaction mixture is refluxed an additional 6 hours, filtered, and the solvent is evaporated to yield 5-(p-formylphenyl)-imidazo[1,5-a]pyridine, m.p. 144°-146°.

Workup

  1. temperaturethe reaction mixture is refluxed an additional 6 hours
  2. filtrationfiltered
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-de6a9596e4b34d389962253cfde21811
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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