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

HRID 1709413Notes

Reaction equation

HRID 1709413 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][CH:18]=[C:17]([Cl:21])[CH:16]=1)C.[OH-].[Na+]>C(O)C.O>[Cl:21][C:17]1[CH: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]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 156171872-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

Product 1

HCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (6.0 g, 0.019 mole), sodium hydroxide pellets (0.9 g, 0.023 mole), and 50 ml of ethanol-water (2:1) was refluxed for 1 hour. The reaction mixture was cooled and the ethanol evaporated in vacuo. The residual aqueous mixture was diluted with water (40 ml) and extracted with diethyl ether (2×25 ml). The aqueous portion was acidified with concentrated hydrochloric acid to a pH of 5-6. After precipitation was complete, the solid was collected by filtration, giving 5.9 g (100%). Recrystallization from ethanol gave 4.7 g of cream colored needles, mp 214°-216° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. customthe ethanol evaporated in vacuo
  4. additionThe residual aqueous mixture was diluted with water (40 ml)
  5. extractionextracted with diethyl ether (2×25 ml)
  6. customAfter precipitation
  7. filtrationthe solid was collected by filtration
  8. customgiving 5.9 g (100%)
  9. customRecrystallization from ethanol
  10. customgave 4.7 g of cream colored needles, mp 214°-216° C.

Sources & evidence

ORD record
ord-cf83f049cb414b448f4ab50982a933c6
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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