Réaction #44230

ord-99b7cf4d4099400eb317131ba24131a7

Équation de réaction

Cl
HCl
CCOC(=O)c1c(Cl)c(C)c(=O)n(C)c1C(C)=O
2-acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester
[Li+].[OH-]
LiOH
→
CC(=O)c1c(C(=O)O)c(Cl)c(C)c(=O)n1C
desired product
CC(=O)c1c(C(=O)O)c(Cl)c(C)c(=O)n1C
2-acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Réactifs

Cl
HCl
CCOC(=O)c1c(Cl)c(C)c(=O)n(C)c1C(C)=O
2-acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester
[Li+].[OH-]
LiOH

Réactifs

Aucun

Solvants

C1CCOC1.O
THF water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionextracted with ethyl acetate
  2. 2
    SéchageThe combined organic extracts are dried (MgSO4)
  3. 3
    Concentrationconcentrated under reduced pressure

Mode opératoire

To a solution of 2-acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 equivalent) in THF:water (4:1) is added 1 M aqueous LiOH solution (2.05 equivalents). After 30 minutes, the reaction mixture is acidified to pH ˜1 with 1 N HCl solution and extracted with ethyl acetate. The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give the desired product which is used directly without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07732616B2uspto-grants-2010_06