Hydrochloric Acid → HCID 22388232, compound

HRID 1072793Notes

Reaction equation

HRID 1072793 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11](C#N)=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:16].[OH-].[Na+].Cl.[C:25](=[O:28])([O-])[OH:26].[Na+]>C(O)C>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:25]([OH:26])=[O:28])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 516892Sodium BicarbonateHCID 22388114HCID 22388114, compound

Product 1

HCID 22388232HCID 22388232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-(2,4-dichlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrile (113 mg) in ethanol (0.6 ml) was added a 30% aqueous sodium hydroxide solution (0.3 ml), and the mixture was refluxed under heating for 12 hr. After 12 hr, a 30% aqueous sodium hydroxide solution (0.5 ml) was added and the mixture was refluxed under heating 3 hr. The reaction mixture was cooled, adjusted to pH 1 with 6N hydrochloric acid, stirred for 1 hr and adjusted to pH 4 with a saturated aqueous sodium hydrogencarbonate solution. The precipitated crystals were collected by filtration to give the objective compound (144 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 12 hr
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating 3 hr
  5. temperatureThe reaction mixture was cooled
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-1736f623cd1b4987ad6f1f67ca34ede8
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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