5-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine → 4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzoic acid

HRID 568533Notes

Reaction equation

HRID 568533 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]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]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 136882135-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Product 1

HCID 136882154-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.66 g of 5-(p-ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 8.0 ml of ethanol and 8.0 ml 1N sodium hydroxide is refluxed for 3 h, cooled and evaporated. The residue is partitioned between water and ethyl acetate. The aqueous phase is adjusted to pH 5 with concentrated sulfuric acid and the solid is filtered and air-dried to yield the title compound, m.p. 309°-310° (dec.).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue is partitioned between water and ethyl acetate
  4. filtrationthe solid is filtered
  5. customair-dried

Sources & evidence

ORD record
ord-e571ff0f614346fab183b0739f3adaa2
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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