Sodium Hydroxide → 2-(4-Chloro-2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 2072937Notes

Reaction equation

HRID 2072937 reaction equation
C([O:3][C:4](=[O:22])[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]=[C:19]([Cl:21])[CH:18]=[CH:17][N:16]=1)C.[OH-].[Na+]>C(O)C.O>[Cl:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([C:7]2[N:6]([CH2:5][C:4]([OH:22])=[O:3])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 156171842-(4-Chloro-2-pyridinyl)3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

Product 1

HCID 156171852-(4-Chloro-2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acidYield 58.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-chloro-2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (1.6 g, 0.005 mole), and crushed sodium hydroxide (0.2 g, 0.005 mole) in aqueous ethanol (5 ml water and 4 ml ethanol) was heated at reflux for 1/2 hr. The reaction mixture was diluted with water (10 ml) and extracted with ether (2×). The aqueous layer was acidified with 3N hydrochloric acid. The precipitate was collected, washed with water, and dried under high vacuum at 50° C. overnight to give 0.84 g of crystals, mp 218°-20° C. with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1/2 hr
  3. extractionextracted with ether (2×)
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-3bc9f0739a3a4d3792a24803fcdaead9
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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