Acetone → 2-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester

HRID 422801Notes

Reaction equation

HRID 422801 reaction equation
[CH2:1]([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]#[C:17][Si](C)(C)C)=[O:5])[CH3:2].[OH:22]S(O)(=O)=O.CC(C)=O>O>[CH2:1]([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:22])[CH3:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 666748954-Chloro-1,5-dimethyl-6-oxo-2-trimethylsilanylethynyl-1,6-dihydropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 666740212-Acetyl-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-1,5-dimethyl-6-oxo-2-trimethylsilanylethynyl-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 equivalent), HgSO4 (1.00 equivalent) and H2SO4 (2.00 equivalents) in 6:1 acetone:water is refluxed for 3 hours. The reaction mixture is cooled to room temperature and concentrated under reduced pressure. The residue is diluted with a mixture of THF and ethyl acetate and washed with water and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure. The desired product is obtained by flash column chromatography as necessary.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is diluted with a mixture of THF and ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74ac0708fe7a4058bafeb01b1c2b93a7
Source dataset
uspto-grants-2012_01
Patent number
US08101639B2

Reaction notes

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