Ethanol → HCID 15617192, compound

HRID 621871Notes

Reaction equation

HRID 621871 reaction equation
C([O:3][C:4](=[O:25])[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][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)C.[OH-].[K+].C(O)C>O>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:19]=[CH:20][C:15]([C:7]2[N:6]([CH2:5][C:4]([OH:25])=[O:3])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14390474HCID 14390474, compound

Product 1

HCID 15617192HCID 15617192, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-[4-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (17.7 g, 0.051 mole), potassium hydroxide pellets (4.5 g, 0.080 mole), 95% ethanol (150 ml), and water (10 ml) was refluxed for 21/2 hrs. The ethanol was evaporated in vacuo, the residue acidified with glacial acetic acid, and the mixture filtered. The filter cake was suspended in water (300 ml) and filtered. The filter cake was air dried (17 g) and recrystallized from ethanol-water to give 12.21 g (75%) of a white solid, mp 240°-241° C.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. filtrationthe mixture filtered
  3. filtrationfiltered
  4. customdried (17 g)
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-f4789b6cf3724b64a7136654b6617469
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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