Hydrochloric Acid → Karetazan

HRID 986570Notes

Reaction equation

HRID 986570 reaction equation
[CH2:1]([N:3]1[C:12]([CH3:13])=[CH:11][C:10](=[O:14])[C:5]([C:6]([O:8]C)=[O:7])=[C:4]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([N:3]1[C:12]([CH3:13])=[CH:11][C:10](=[O:14])[C:5]([C:6]([OH:8])=[O:7])=[C:4]1[C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14075279Methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate

Product 1

HCID 157722KaretazanYield 95.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

46.1 g of crude methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate is suspended in 600 ml of 5% aqueous NaOH solution and warmed to 80°-85°. After 1-11/2 hours at this temperature the reaction mixture is cooled and acidified with dilute HCl. The resulting solid precipitate is collected by filtration, yielding 42 g of 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinic acid, mp (methylene chloride/ether)=235°-237° C.

Workup

  1. temperaturewarmed to 80°-85°
  2. temperatureAfter 1-11/2 hours at this temperature the reaction mixture is cooled
  3. filtrationThe resulting solid precipitate is collected by filtration

Sources & evidence

ORD record
ord-c6312fee139a49598e472b9375cf9c5c
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

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