Potassium Hydroxide → HCID 14390329, compound

HRID 1709521Notes

Reaction equation

HRID 1709521 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=[C:12]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)C.[OH-].[K+]>C(O)C>[OH2:3].[Cl:26][C:22]1[CH:21]=[C:20]([C:12]2[N:11]([CH2:10][C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])=[O:27])[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14390263HCID 14390263, compound

Product 1

HCID 14390329HCID 14390329, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[[(2-(3-chlorophenyl)-3H-imidazo[4,5-b] pyridine-3-yl]acetyl]amino]butanoic acid ethyl ester (2.4 g, 0.006 mole) and potassium hydroxide (0.5 g) in 100 ml of ethanol was heated at reflux for 2 hrs. The reaction mixture was evaporated to dryness. The residue was dissolved in water, filtered, and the filtrate was acidified with acetic acid. The precipitate, which had formed, was collected by filtration, washed with water, and dried. The solid was recrystallized from ethanol-water, collected by filtration, washed with water, and dried under high vacuum at 78° C. over 2 days to give 0.93 g (42%), mp 207°-8° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. filtrationfiltered
  6. customThe precipitate, which had formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried
  10. customThe solid was recrystallized from ethanol-water
  11. filtrationcollected by filtration
  12. washwashed with water
  13. customdried under high vacuum at 78° C. over 2 days
  14. customto give 0.93 g (42%), mp 207°-8° C.

Sources & evidence

ORD record
ord-8f53dea58a84451cb12705f3600a1d85
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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