Hydrochloric Acid → 4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1020207Notes

Reaction equation

HRID 1020207 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([O:13]CC)=[O:12])=[CH:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].CO.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[CH:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 11680224Ethyl 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 115429654-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (172 mg, 0.75 mmol) dissolved in a 4:1 mixture of THF:MeOH (5 mL) (v:v), was added a aqueous solution of LiOH (1.52 mmol, 1M). After stirring for 40 min, the reaction mixture was acidified to pH˜1 with HCl(1N, aq) and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered and concentrated under the reduced pressure to give an off-white solid as the title compound. (163 mg, 100% yield).

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-b050c59c0bcd478592528b5117376503
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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