Hydrochloric Acid → 4-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 2351617Notes

Reaction equation

HRID 2351617 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]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)C.[OH-].[Na+].C(O)C.O.Cl>O>[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:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15617197HCID 15617197, compoundHCID 19096565Water ethanol

Product 1

HCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acidYield 111.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.6 g (0.04 mole) of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester, 2.9 g (0.073 mole) of sodium hydroxide pellets, and 150 ml of ethanol/water (1:1) was refluxed for 45 min. The reaction mixture was poured into a 250-ml of water, acidified with concentrated hydrochloric acid; and filtered, giving 12.8 g (97%) of a white solid. A 2-g portion was recrystallized from methanol-water to give 1.2 g of white needles, mp 271°-273° C. with decomposition.

Workup

  1. temperaturewas refluxed for 45 min
  2. filtrationand filtered

Sources & evidence

ORD record
ord-85dd9bff2fad405480087e31a08657f2
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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