HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-(2-Chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | 2-(2-Chloro-4-methoxy-phenyl)-3-(2-methyl-pyridin-4-yl)-3-oxo-propionic acid methyl ester | HCID 66699183 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-(2-Chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-ethanone | HCID 66699088 | 65.6% |
Reaction Conditions
| Temperature | 140 °C |
|---|
Reaction Steps
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+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08138189B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-4a2d47ee959043fe997059f526e42777 |
| Source note | uspto-grants-2012_03 |