ethyl 4-(H-imidazo[1,5-a]pyridin-5-yl)benzoate → 5-(p-Carboxyphenyl)imidazo[1,5-a]pyridine

HRID 280215Notes

Reaction equation

HRID 280215 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C>C(O)C.[OH-].[Na+]>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 13649431ethyl 4-(H-imidazo[1,5-a]pyridin-5-yl)benzoate

Product 1

HCID 136882245-(p-Carboxyphenyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-(p-ethoxycarbonylphenyl)-imidazo[1,5-a]pyridine (1.0 g) in 10 ml of ethanol and 10 ml of 1N sodium hydroxide is refluxed for 3 hours. The ethanol is evaporated. The aqueous phase is washed with ether, adjusted to pH=6 and the solid collected to yield 5-(p-carboxyphenyl)imidazo[1,5-a]pyridine.

Workup

  1. customThe ethanol is evaporated
  2. washThe aqueous phase is washed with ether
  3. customthe solid collected

Sources & evidence

ORD record
ord-7706647bea924dc8a726ba0ea88b11ee
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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