Hydrochloric Acid → 2-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1510587Notes

Reaction equation

HRID 1510587 reaction equation
C([O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10]([CH3:13])[C:9](=[O:14])[N:8]([CH3:15])[C:7]=1[C:16](=[O:18])[CH3:17])=[O:5])C.[Li+].[OH-].Cl>C1COCC1.O>[C:16]([C:7]1[N:8]([CH3:15])[C:9](=[O:14])[C:10]([CH3:13])=[C:11]([Cl:12])[C:6]=1[C:4]([OH:5])=[O:3])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 666740212-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 666739552-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

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.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts are dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0502484b74bf4309becfec5785c3dddb
Source dataset
uspto-grants-2012_07
Patent number
US08211921B2

Reaction notes

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