Sodium Hydroxide → HCID 14390453, compound

HRID 2351618Notes

Reaction equation

HRID 2351618 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]=[CH:17][C:16]=1[Cl:21])C.[OH-].[Na+]>C(O)C.O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:7]1[N:6]([CH2:5][C:4]([OH:22])=[O:3])[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15617186HCID 15617186, compound

Product 1

HCID 14390453HCID 14390453, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 9.7 g (0.0308 mole) of 2-(2-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester, 2.5 g (0.0339 mole) of sodium hydroxide (pellets), and 100 ml of ethanol-water (1:1) was refluxed for 1 hr. The ethanol was evaporated and the residual aqueous solution was extracted with methylene chloride (2×30 ml). The aqueous layer was acidified with concentrated hydrochloric acid and filtered. The filter cake was recrystallized from ethanol-water to give 7.0 g (79%). A 2.0-g portion was recrystallized from ethanol-isopropyl ether to give white needles, mp 227°-228° C.

Workup

  1. temperaturewas refluxed for 1 hr
  2. customThe ethanol was evaporated
  3. extractionthe residual aqueous solution was extracted with methylene chloride (2×30 ml)
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from ethanol-water
  6. customto give 7.0 g (79%)
  7. customA 2.0-g portion was recrystallized from ethanol-isopropyl ether
  8. customto give white needles, mp 227°-228° C.

Sources & evidence

ORD record
ord-88a69328c447448e93226117323644fd
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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