Naphthalene addition compound with mercuric

In a 2-1. round-bottom flask, equipped with a stirrer, are placed 231 g. (0.5 mole) of the addition compound of /3-naphthalene diazonium chloride and mercuric chloride (p. 55), 700 cc. of acetone (b.p. 55-57°) and 189 g. (3 moles) of copper powder (Note 1). The mixture is quickly cooled to 20° and stirred for one hour. The mixture is treated with 700 cc, of concentrated aqueous ammonia solution (sp. gr. 0.9), mixed well, and allowed to stand overnight. The supernatant liquid is decanted the solid is collected on a Buchner funnel and washed successively with 25-cc. portions of water, acetone, and ether. After airdrying, the crude material is recrystallized from xylene, using decolorizing carbon. The crystals thus obtained are slightly yellow (Note 2) and melt at 241.5-243.50. The yield is 51-55 g. (45-48 per cent of the theoretical amount based on the addition compound used). 

To 450 cc. of concentrated hydrochloric acid (sp. gr. 1.19) and 500 cc. of water in a 4-I. (i-gal.) earthenware crock equipped with an efficient stirrer is added 143 g. (1 mole) of /3-naphthyla-mine. The suspension of the amine hydrochloride is cooled by the addition of 500 g. of cracked ice. When the temperature reaches 5° solid sodium nitrite (about 69 g.) is added until starch-iodide paper shows an excess. During the diazotization about 600 g. of cracked ice is introduced at such a rate as to keep the temperature at 50. The cold solution of the diazonium salt is filtered to remove a small amount of precipitate and returned to the crock. A solution of 271 g. (1 mole) of mercuric chloride in 300 cc. of concentrated hydrochloric acid is mixed with 300 g. of ice and added slowly to the rapidly stirred solution. A heavy yellow solid separates. Stirring is continued for one-half hour to secure complete reaction. The yellow addition compound of /3-naphthalene diazonium chloride and mercuric chloride is collected on a 20-cm. Buchner funnel, sucked as dry as possible, and then washed with two 400-cc. portions of water and two 150-cc. portions of acetone (Note 1). The... 

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