Sodium Hydroxide → HCID 14075347, compound

HRID 2107909Notes

Reaction equation

HRID 2107909 reaction equation
[OH-].[Na+].Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:26])[C:13]([CH2:23][CH2:24][CH3:25])=[C:14]([C:20](=[O:22])[CH:21]=2)[C:15]([O:17]CC)=[O:16])=[CH:7][CH:6]=1>O.C(O)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]([CH3:26])[C:13]([CH2:23][CH2:24][CH3:25])=[C:14]([C:20](=[O:22])[CH:21]=2)[C:15]([OH:17])=[O:16])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14075387HCID 14075387, compound

Product 1

HCID 14075347HCID 14075347, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.0 g (0.05 mol) of 50% aqueous sodium hydroxide is added to a suspension of 2.7 g (0.01 mol) ethyl 6-(4-chlorophenyl)-1-methyl-2-n-propyl-4-oxonicotinate hydrochloride in 50 ml of water and 10 ml of ethanol. The mixture is refluxed and stirred for 3 hrs, allowed to stand at room temperature for 18 hrs., refluxed for an additional 1 hr. and cooled to room temperature. The solution formed is extracted with three 50 ml portions of methylene dichloride and the aqueous solution is acidified to pH 1 with 12N hydrochloric acid. The suspension formed is stirred at room temperature for 3 hrs. and is vacuum filtered. The filter cake is dried to afford 1.65 g (54% yield) of 6-(4-chlorophenyl)-1-methyl-2-n-propyl-4-oxonicotinic acid, mp 184°-187° C.

Workup

  1. temperatureThe mixture is refluxed
  2. waitto stand at room temperature for 18 hrs
  3. temperature, refluxed for an additional 1 hr
  4. customThe solution formed
  5. extractionis extracted with three 50 ml portions of methylene dichloride
  6. customThe suspension formed
  7. stirringis stirred at room temperature for 3 hrs
  8. filtrationfiltered
  9. customThe filter cake is dried

Sources & evidence

ORD record
ord-3f8ead6d295743a4ac88f20f519a6c17
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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