Sodium Hydroxide → HCID 14075329, compound

HRID 2107905Notes

Reaction equation

HRID 2107905 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH3:23])[C:12]([CH3:22])=[C:13]([C:19](=[O:21])[CH:20]=2)[C:14]([O:16]CC)=[O:15])=[CH:6][CH:5]=1>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]([CH3:23])[C:12]([CH3:22])=[C:13]([C:19](=[O:21])[CH:20]=2)[C:14]([OH:16])=[O:15])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14075327HCID 14075327, compound

Product 1

HCID 14075329HCID 14075329, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 g (0.019 mol) of 50% aqueous sodium hydroxide is added to a suspension of 2.9 g (0.0095 mol) ethyl 6-(4-chlorophenyl)-1,2-dimethyl-4-oxonicotinate in 75 ml of water. The mixture is refluxed and stirred for 15 min. and cooled to room temperature. The solution is extracted with methylene dichloride and the aqueous solution is acidified to pH 1 with 12N hydrochloric acid. The suspension formed is vacuum filtered and the filter cake is dried to afford 1.8 g (68% yield) of 6-(4-chlorophenyl)-1,2-dimethyl-4-oxonicotinic acid, mp 236°-238° C. dec.

Workup

  1. temperatureThe mixture is refluxed
  2. extractionThe solution is extracted with methylene dichloride
  3. customThe suspension formed
  4. filtrationfiltered
  5. customthe filter cake is dried

Sources & evidence

ORD record
ord-8c939a788e80463d965c03c9187b4f36
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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