Ethanol → HCID 15617180, compound

HRID 2351623Notes

Reaction equation

HRID 2351623 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)C.[OH-].[K+].C(O)C>O>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:7]1[N:6]([CH2:5][C:4]([OH:21])=[O:3])[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15617179HCID 15617179, compound

Product 1

HCID 15617180HCID 15617180, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (18.0 g, 0.064 mole), potassium hydroxide pellets (5.6 g, 0.100 mole), 95% ethanol (250 ml) and water (10 ml) was refluxed for 11/2 hr. The solution was evaporated to 1/3 volume and then diluted with water (50 ml) and acidified with glacial acetic acid. Water (200 ml) was added and the mixture filtered after precipitation was complete, giving 15.5 g (96%) of a granular solid. Recrystallization of a 2.0-g portion twice from ethanol-water gave 1.5 g of an off-white granular solid, mp 224°-225° C. with decomposition.

Workup

  1. customThe solution was evaporated to 1/3 volume
  2. additiondiluted with water (50 ml)
  3. additionWater (200 ml) was added
  4. filtrationthe mixture filtered
  5. customafter precipitation

Sources & evidence

ORD record
ord-130ccb30356a4530bdc45a755f9faa6e
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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