Water → 2-(2-Chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-ethanone

HRID 1095922Notes

Reaction equation

HRID 1095922 reaction equation
COC(=O)[CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[Cl:22])[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1)=[O:6].[Cl-].[Na+].O>CS(C)=O>[Cl:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 666991832-(2-Chloro-4-methoxy-phenyl)-3-(2-methyl-pyridin-4-yl)-3-oxo-propionic acid methyl ester

Product 1

HCID 666990882-(2-Chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-ethanoneYield 65.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(2-chloro-4-methoxy-phenyl)-3-(2-methyl-pyridin-4-yl)-3-oxo-propionic acid methyl ester (13.95 g), sodium chloride (2.71 g), water (1.14 mL) and DMSO (400 mL) was heated to 140° C. for 3 hours. Stirring was continued overnight at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a yellow solid (7.56 g, 62%). MS (m/e)=276.2 [MH+].

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-4a2d47ee959043fe997059f526e42777
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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