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

HRID 1366088Notes

Reaction equation

HRID 1366088 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-ac40699cb0f44211b7ac50f0236b0ac1
Source dataset
uspto-grants-2011_02
Patent number
US07893065B2

Reaction notes

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