Reaction #78158

Reaction equation

1-chloro-4-(4-pyridylmethyl)phthalazine

p-toluidine

acetate

→

Title compound

1-(4-Methylanilino)-4-(4-pyridylmethyl)phthalazine

Solvents

potassium carbonate

Conditions

Workup

1. 1
   WashThe organic phase washed with water
2. 2
   Dryingdried over anhydrous sodium sulfate
3. 3
   Otheris evaporated
4. 4
   Otherthe residue purified on silica gel by flash chromatography

Procedure

A mixture of 0.384 g (1.5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.482 g (4.5 mmol) p-toluidine is stirred for 1.5 h at 90° C. under a nitrogen atmosphere. The reaction mixture is then distributed between 30 ml acetate and 20 ml of 20% aqueous potassium carbonate solution. The organic phase washed with water and dried over anhydrous sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol mixtures (50:1 to 9:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile and drying under HV; m.p. 152-153° C.; ESI-MS: (M+H)+=327.

Source