Potassium Hydroxide → HCID 14676660, compound

HRID 2351628Notes

Reaction equation

HRID 2351628 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)C.[OH-].[K+]>C(O)C.O.CO>[OH2:3].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[N:6]([CH2:5][C:4]([OH:22])=[O:3])[C:14]3[C:9]([N:8]=2)=[N:10][CH:11]=[CH:12][CH:13]=3)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 14390437HCID 14390437, compound

Product 1

HCID 14676660HCID 14676660, compoundYield 3.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetic acid ethyl ester (8.4 g, 0.027 mole) and potassium hydroxide (2.25 g, 0.04 mole) in 95% ethanol (75 ml) and water (5 ml) was heated at reflux for 2.5 hours. The mixture was evaporated to dryness. The residue was dissolved in water and acidified with glacial acetic acid. The precipitate was collected by filtration, washed with water, and dried under high vacuum overnight at 60° C. to give 7.4 g (95%) yield). A 1.4-g sample was dissolved in ~450 ml of boiling methanol, and the solution was treated with Florsil® and filtered. The filtrate was concentrated and diluted with water. A crystalline precipitate was collected by filtration, washed with water, and dried under high vacuum at 60° C. for 4 hours, then at room temperature over the weekend to give 0.16 g of solids, mp. 194°-96° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customThe mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried under high vacuum overnight at 60° C.
  8. customto give 7.4 g (95%)
  9. customyield)
  10. additionthe solution was treated with Florsil®
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated
  13. additiondiluted with water
  14. filtrationA crystalline precipitate was collected by filtration
  15. washwashed with water
  16. customdried under high vacuum at 60° C. for 4 hours

Sources & evidence

ORD record
ord-7715de9cbd2e4064b481cd2d4aea883f
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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