Potassium Hydroxide → HCID 14676660, compound

HRID 621874Notes

Reaction equation

HRID 621874 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+].[O-][Si]([O-])=O.[Mg+2]>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

7

Reactant 3

HCID 14797Potassium HydroxideHCID 61680MAGNESIUM SILICATE (synthetic)HCID 14390437HCID 14390437, compound

Product 1

HCID 14676660HCID 14676660, compoundYield 95%

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 Florisil® 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% yield)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. additiondiluted with water
  12. filtrationA crystalline precipitate was collected by filtration
  13. washwashed with water
  14. customdried under high vacuum at 60° C. for 4 hours

Sources & evidence

ORD record
ord-4e160616d99f47b5a99906fb23c880da
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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