ethyl benzenesulfonate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.4 g of 2-hydroxy-3-chloro-5-methyl-N-methyl-N-cyclooctylbenzylamine were dissolved in 40 ml of hot absolute ethanol and added to a sodium ethylate solution that had been prepared from 0.6 g of sodium in 25 ml of absolute ethanol. After addition of 4.5 g of benzenesulfonic acid ethyl ester, the whole was stirred for 5 hours under reflux, concentrated, the residue was dissolved in 50 ml of 5% sodium hydroxide solution, extracted with ether and the organic phase was dried over sodium sulfate. The solvent was removed and after addition of 70 ml of water and hydrochloric acid until acid reaction the residue was covered with 50 ml of ether and allowed to stand for several days at 0° C. In this manner, 6 g of 2-ethoxy-3-chloro-5-methyl-N-methyl-N-cyclooctyl-benzylamine-hydrochloride were obtained. Melting point 197° C (ethanol/ether). under reflux concentrated the residue was dissolved in 50 ml of 5% sodium hydroxide solution extracted with ether the organic phase was dried over sodium sulfate The solvent was removed after addition of 70 ml of water and hydrochloric acid until acid reaction the residue to stand for several days at 0° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.06 g (0.1 mole) of 3-amino-7-chloro-4-quinoline-thiol are dissolved in 100 ml of a 2 molar sodium hydroxide solution, whereupon 23.30 g (0.125 mole) of ethyl benzene sulfonate are added. The reaction mixture is heated to boiling for 2 hours and the product thus formed is extracted with chloroform. The chloroform solution is clarified with activated charcoal, dried and acidified with alcohol containing hydrogen chloride. Thus 24.0 g of 3-amino-4-ethylthio-7-chloro-quinoline-hydrochloride are obtained. After crystallization from methanol the product melts at 212°-216° C. under decomposition. Yield 85%. The product thus obtained is identical with the compound prepared according to Example 5. are added The reaction mixture is heated the product thus formed is extracted with chloroform dried containing hydrogen chloride