Hydrochloric Acid → HCID 22388232, compound

HRID 1699813Notes

Reaction equation

HRID 1699813 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-f194ac02475540898a097d578d7876bf
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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