Ethylene Glycol → (S)-2-(4-Chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid 2-hydroxyethyl ester

HRID 1709581Notes

Reaction equation

HRID 1709581 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].O.[CH2:28](O)[CH2:29][OH:30]>S(=O)(=O)(O)O>[OH:30][CH2:29][CH2:28][O:19][C:18](=[O:20])[C@H:17]([CH3:21])[N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 516892Sodium BicarbonateHCID 14390427(S)-2-(4-chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390431(S)-2-(4-Chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid 2-hydroxyethyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.0 g, 0.00995 mole) and concentrated sulfuric acid (4 drops) in ethylene glycol (50 ml) was refluxed under nitrogen for three hours, and then poured into a saturated sodium bicarbonate solution (200 ml). Water (50 ml) was added and the product was extracted into two portions of ethyl acetate. The combined organic layers were washed twice with water and once with a saturated sodium chloride solution, dried over magnesium sulfate, treated with charcoal and filtered. Evaporation of the solvents under reduced pressure gave 1.9 g (56% yield) of solid which was dissolved in hot isopropyl ether (with a little isopropyl alcohol added). The solution was stirred and cooled to room temperature to precipitate a solid. The mixture was cooled in the freezer, the solid was collected by filtration, rinsed with isopropyl ether and dried under high vacuum at room temperature overnight to give 1.44 g of title compound, mp 112°-113.5° C.

Workup

  1. extractionthe product was extracted into two portions of ethyl acetate
  2. washThe combined organic layers were washed twice with water and once with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-ff53a641ee554dad8ba5aeb07d1b291e
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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