Methanol → Methyl 3-(2-chloro-4-hydroxybenzyl)-2,7-dimethylimidazo[4,5-b]pyridine-5-carboxylate

HRID 2181025Notes

Reaction equation

HRID 2181025 reaction equation
C([O:4][C:5]1[CH:26]=[CH:25][C:8]([CH2:9][N:10]2[C:14]3=[N:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][C:18]([CH3:19])=[C:13]3[N:12]=[C:11]2[CH3:24])=[C:7]([Cl:27])[CH:6]=1)(=O)C.S(=O)(=O)(O)O.CO>C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>[Cl:27][C:7]1[CH:6]=[C:5]([OH:4])[CH:26]=[CH:25][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][C:18]([CH3:19])=[C:13]2[N:12]=[C:11]1[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22485009methyl 3-(4-acetoxy-2-chlorobenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate

Product 1

HCID 22485017Methyl 3-(2-chloro-4-hydroxybenzyl)-2,7-dimethylimidazo[4,5-b]pyridine-5-carboxylateYield 65.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of methyl 3-(4-acetoxy-2-chlorobenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (6.5 g), conc. sulfuric acid (3.0 ml) and methanol (60 ml) was refluxed under heating for 1.5 hr. The reaction mixture was diluted with chloroform (60 ml) and saturated aqueous sodium hydrogen carbonate solution was gradually added under ice-cooling. The organic layer was separated, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was washed with diethyl ether to give methyl 3-(2-chloro-4-hydroxybenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (3.81 g) as a pale-yellow powder.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hr
  3. additionwas gradually added under ice-
  4. temperaturecooling
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-0a899e7c97064d209c034ac675d93393
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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