Potassium Hydroxide → HCID 14390329, compound

HRID 621970Notes

Reaction equation

HRID 621970 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-240c108ddc524dcfae4a324f7a9459c2
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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