Of p-cyanobenzenesulfonamide with Raney nickel alloy

Cyanoanthracene, 50,55 p-Cyanobenzenesulfonamide, reduction with Raney nickel alloy to p-for-mylbenzenesulfonamide, 51,20 p-Cyano-N,N-diethylaniline, 50, S4 Cyanohydrins, formation by use of alkyl-aluminum cyanides, 52, 96... 

A 2-1. two-necked round-bottomed flask fitted with a mechanical stirrer and a reflux condenser is charged with 40.0 g. (0.22 mole) of p-cyanobenzenesulfonamide (Note 1), 600 ml. of 75% (v/v) formic acid, and 40 g. of Raney nickel alloy (Note 2). The stirred mixture is heated under reflux for 1 hour (Note 3). The mixture is filtered with suction through a Buchner funnel coated with a filter aid (Note 4), and the residue on the funnel is washed with two 160-ml. portions of 95% ethanol. The combined filtrates are evaporated under reduced pressure with a rotary evaporator (Note 5). The solid residue (Note 6) is heated in 400 ml. of boiling water and freed from a small amount of insoluble material by decantation through a plug of glass wool placed in a filter funnel. The filtrate is chilled in an ice bath and the precipitate is collected by filtration with miction, washed with a small amount of cold water and dried at 50°... 

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