3-Chloro-6-nitroacetanilide

A mixture of 6.65 g of 3-chloro-6-nitroacetanilide, 3.2 ml of propylmercaptan, 5.6 g of 50% sodium hydroxide and 100 mi of water Is heated at reflux overnight. The cooled mixture is filtered to give the desired 2-nitro-5-propyithioaniline, MP 69.5°-71.5°C after recrystailiza-tion from ethanoi then hexane-ether. NMR (CDCi3) 40%. 

Various nitrosoarenes have been utilized as benzofurazan precursors including o-azido derivatives generated from the o-chloro analogues <66JCS(B)1004>, and 1-amino-2-nitrosoarenes which can be oxidized with ferricyanide or hypochlorite. Treatment of o-nitrosophenols with hydroxylamine also affords the furazan, presumably via an oximation-dehydration pathway involving the tautomeric o-quinone monooxime. Other related approaches involve the reduction of o-dinitroarenes with borohydride, and the thermolysis of o-nitroanilines and o-nitroacetanilides. 

A mixture of 114.0 g (0.587 m) of N-methyl-4-nitroacetanilide and 800 ml of ethanol was shaken with hydrogen over one teaspoon of Raney active nickel catalyst in water. A pressure drop of 127 psi was recorded (calc. 118 psi). The catalyst was removed by filtration and the ethanol filtrate refluxed overnight with 127.0 g (0.587 m) of the 9-chloro-7-methylimidazo[4,5-f]quinolone. The mixture was chilled, filtered, washed with ether and air-dried to give 75.5 g of 9-[p-(N-methylacetamido)anilino]-7-methyl-l-H-imidazo[4,5-f] quinoline... 

H-Et see 5-Chloro-2-nitro-iV-ethylaniline. "S-Acetyl 5 - chloro - o - nitroacetanilide. 

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