Reaktion #8320

Reaktionsgleichung

hydrochloric acid

3-chloro-4-fluorophenylacetonitrile

6-methyl-pyridine-2-carboxylic acid methyl ester

sodium hydride

→

title compound

2-(3-Chloro-4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is refluxed for 2.5 h
2. 2
   EinengenThe mixture is concentrated in vacuo
3. 3
   workup.ADDITIONConcentrated hydrochloric acid (50 mL) is added to the mixture after which it
4. 4
   Temperaturis refluxed for 1.5 h
5. 5
   workup.ADDITIONThe mixture is poured over ice
6. 6
   ExtraktionThe mixture is extracted with methylene chloride
7. 7
   Trocknenthe organic portions dried over anhydrous sodium sulfate
8. 8
   FiltrationThe mixture is filtered
9. 9
   Einengenconcentrated in vacuo

Vorschrift

A dispersion of sodium hydride, (60% in mineral oil, 0.7 g, 17.7 mmol) is added to ethanol (25 mL). When gas evolution ceases, 3-chloro-4-fluorophenylacetonitrile (Fluorochemicals, 2.0 g, 11.8 mmol) and 6-methyl-pyridine-2-carboxylic acid methyl ester (1.8 g, 11.8 mmol), are added. The mixture is refluxed for 2.5 h and adjusted to pH 7 with 1 N hydrochloric acid. The mixture is concentrated in vacuo. Concentrated hydrochloric acid (50 mL) is added to the mixture after which it is refluxed for 1.5 h. The mixture is poured over ice and adjusted to pH 8 with 5 N sodium hydroxide. The mixture is extracted with methylene chloride and the organic portions dried over anhydrous sodium sulfate. The mixture is filtered and concentrated in vacuo to yield the title compound, 2.1 g (68%), as a yellowish solid.

Quelle