O-Xylene → HCID 178515186, compound

Participants

Reaction Steps

The mixture of 1,681 g of ethyl 4-chloro-quinoline-3-carboxylate, 1,017 g of p-chlorophenylhydrazine and 25 L of xylene is heated to 105° for 24 hours while stirring under nitrogen. The resulting suspension is cooled to 20°, combined with 14 L of 2 N aqueous sodium hydroxide, stirred for 15 minutes and diluted with 30 L of water. Stirring is continued for 1 hour, the aqueous phase separated, washed five times with 8 L of diethyl ether each, filtered and the filtrate treated with the solution of 1,600 g of ammonium chloride in 8 L of water while stirring under nitrogen. The resulting suspension is stirred overnight at room temperature, filtered and the residue washed 5 times with 12 L of hot water. This residue is dried at 5 mmHg and 90° and 1,665 g thereof are dissolved in 8.4 L of dimethylformamide at 130°. The solution is filtered and allowed to cool to room temperature while stirring. The resulting suspension is filtered, washed twice with 500 ml of cold dimethylformamide each, four times with 1 L of diethyl ether and the residue is dried at 0.1 mmHg and 100°, to yield the 2-(p-chlorophenyl)-pyrazolo[4,3-c]quinolin-3(5H)-one of the formula ##STR9## melting at 324°-327° with decomposition.

Provenance & Evidence