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

HRID 477976Notes

Reaction equation

HRID 477976 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 1.18 g or 5-(p-ethoxycarbonylphenyl)imidazo[1,5-a]pyridine in 10 ml of ethanol and 14 ml of 1N sodium hydroxide solution is refluxed for 3 h, cooled and evaporated. The residue is partitioned between water and ethyl acetate. The aqueous phase is separated and adjusted to pH 5. The solid is filtered, washed with water and dried to yield the title compound, m.p. 308°-310° (dec.).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue is partitioned between water and ethyl acetate
  4. customThe aqueous phase is separated
  5. filtrationThe solid is filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-893e4ff13bdf4ee080b2bc2d6c15f3c4
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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