Ethanol → HCID 15617192, compound

HRID 1709420Notes

Reaction equation

HRID 1709420 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-fd65fc98e0484cf793aa5244155b1d84
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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