Sodium Hydroxide → HCID 14075339, compound

HRID 2107907Notes

Reaction equation

HRID 2107907 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:22])[C:11]([CH3:21])=[C:12]([C:18](=[O:20])[CH:19]=2)[C:13]([O:15]CC)=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+]>O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH3:22])[C:11]([CH3:21])=[C:12]([C:18](=[O:20])[CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14075381HCID 14075381, compound

Product 1

HCID 14075339HCID 14075339, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.3 g (0.014 mol) of ethyl 6-(4-bromophenyl)-1,2-dimethyl-4-oxonicotinate hydrochloride is suspended in 100 ml of water and to it there is added 5 g (0.0625 mol) of 50% aqueous sodium hydroxide. The mixture is refluxed and stirred for 1 hr. and the solution formed is cooled to room temperature. The solution is extracted with methylenedichloride and the aqueous solution is acidified to pH 1 with 12N hydrochloric acid. The suspension formed is vacuum filtered and the filter cake is washed with water and dried to afford 4 g (89% yield) of 6-(4-bromophenyl)-1,2-dimethyl-4-oxonicotinic acid, mp 269°-271° C. dec.

Workup

  1. temperatureThe mixture is refluxed
  2. customand the solution formed
  3. extractionThe solution is extracted with methylenedichloride
  4. customThe suspension formed
  5. filtrationfiltered
  6. washthe filter cake is washed with water
  7. customdried

Sources & evidence

ORD record
ord-3f11c7ac58b84149811a066698e11102
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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