Glyoxylic acid, monohydrate → HCID 67358291, compound

HRID 1185992Notes

Reaction equation

HRID 1185992 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][N:10]3[CH:19]=2)=[CH:3][CH:2]=1.O.[C:22]([OH:26])(=[O:25])[CH:23]=[O:24]>ClCCl>[OH:24][CH:23]([C:7]1([C:4]2[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=2)[N:8]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]2=[N:10][CH2:19]1)[C:22]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 16088231Methyl 2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 67358291HCID 67358291, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 2-(4-tolyl)imidazo[1,2-a]pyridine-6-carboxylate 3 (13.31 g, 50 mmol) in dichloromethane (100 ml) was added solid glyoxylic acid monohydrate (6 g) and the mixture was heated at reflux for 4 h. The mixture was then cooled to room temperature and the white solid filtered, washed by dichloromethane, and dried under vacuum to give (14.9 g, 87%) of 2-hydroxy-2-[6-methoxycarbonyl-3-(4-tolyl)imidazo[1,2-a]pyridine-3-yl]acetic acid 4 as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationthe white solid filtered
  4. washwashed by dichloromethane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-89348d576d1f483683cb05062f44bda3
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

Loading…