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

HRID 568529Notes

Reaction equation

HRID 568529 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-eac8f2e87e7e4ec68d97ab4acb059182
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

Loading…