Reaktion #78174

Reaktionsgleichung

4-[(2-methyl-pyridin-4-yl)-methyl]-1(2H)-phthalazinone

phosphorus pentoxide

triethylamine hydrochloride

4-chloroaniline

sodium carbonate

→

Title compound

1-(4-Chloroanilino) 4-[(2-methyl-4-pyridyl)methyl]phthalazine

Lösungsmittel

dichloromethane methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehas formed
2. 2
   SonstigeThe cooled reaction mixture
3. 3
   workup.STIRRINGwith thorough stirring
4. 4
   WaschenThe organic phase washed with water and brine
5. 5
   Trocknenis dried over anhydrous sodium sulfate
6. 6
   Sonstigeevaporated under vacuum
7. 7
   Sonstigethe residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm

Vorschrift

A mixture of 910 mg (6.36 mmol) phosphorus pentoxide, 876 mg (6.36 mmol) triethylamine hydrochloride, and 812 mg (6.36 mmol) 4-chloroaniline is heated at 200° C. until a homogeneous melt has formed. To the melt, 400 g (1.59 mmol) 4-[(2-methyl-pyridin-4-yl)-methyl]-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 16 h at 200° C. The cooled reaction mixture is distributed with thorough stirring and use of an ultrasonic bath between a dichloromethane/methanol mixture (about 20:1) and saturated aqueous sodium carbonate solution. The organic phase washed with water and brine is dried over anhydrous sodium sulfate, evaporated under vacuum, and the residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm, using an acetate/methanol mixture (19:1). Title compound is obtained after evaporation of the product-containing fractions under vacuum and crystallization of the residue from acetonitrile; m.p. 158-159° C.; ESI-MS: (M+H)+=361. The starting material is prepared as follows:

Quelle