Hydrochloric Acid → HCID 66665502, compound

Participants

Reaction Steps

9 ml of conc. hydrochloric acid are added to a suspension, cooled to 0° C., of 90.5 g (332 mmol) of 2-(4-methylquinolin-2-yl)phenylamine hydrochloride in 1300 ml of ice-water and 1000 ml of toluene in an open 10 l beaker, and a solution of 24.1 g (352 mmol) of sodium nitrite in 100 ml of water is then added dropwise, during which the temperature is kept below +5° C. When the addition is complete, the mixture is stirred for a further 20 min., a solution of 24.9 g (382 mmol) of sodium azide in 500 ml of ice-water is then allowed to run in slowly with vigorous stirring (note: evolution of gas, foaming!), and the mixture is then stirred further until the evolution of gas is complete. After warming to room temperature, the reaction mixture is rendered slightly alkaline using saturated sodium carbonate solution, the organic phase is separated off, washed once with 500 ml of water and once with 500 ml of saturated sodium chloride solution, dried over a mixture of sodium carbonate and magnesium sulfate, the desiccant is filtered off, and the filtrate is slowly heated to reflux under argon (care: evolution of gas from about 80° C.). After 8 h under reflux, the mixture is allowed to cool, filtered through 800 g of alumina (basic, activity grade 1), rinsed with 2000 ml of toluene, and the filtrate is then evaporated to dryness in vacuo. The yellow oil obtained in this way is recrystallised twice from about 300 ml of ethanol. The solid obtained in this way is freed from readily volatile and non-volatile secondary components by fractional sublimation (p about 1×10−5 mbar, T about 180° C.). Yield: 48.8 g (210 mmol), 63%, purity: about 99.5% (NMR).

Provenance & Evidence