Hydrochloric Acid → 4-Chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 15904Notes

Reaction equation

HRID 15904 reaction equation
C([O:3][C:4]([C:6]1[C:11]([Cl:12])=[CH:10][C:9](=[O:13])[N:8]([CH3:14])[CH:7]=1)=[O:5])C.C1COCC1.[Li+].[OH-].Cl>CO>[Cl:12][C:11]1[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]([CH3:14])[C:9](=[O:13])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11615451Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 116655334-Chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (0.925 g, 4.29 mmol) in a 4:1 mixture of THF:MeOH (20 mL) was added a 1 M solution of LiOH (8.6 mL). After stirring for 30 minutes, the reaction mixture was acidified to pH 1 with 10% HCl and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to give 0.732 g (91%) clean desired product.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f104f44a1da494fae6dd58bdd56d0d5
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Reaction notes

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