- Synthetic Method of Hexahydro-2-(1H)-azocinone
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Hexahydro-2-(1H)-azocinone(CAS no.: ), which is also known as 2(1H)-Azocinone, hexahydro-, could be produced through the following synthetic routes.
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A 100-mL, three-necked flask is equipped with a magnetic stirring bar, a pressure-equalizing dropping funnel, and a reflux condenser connected to a nitrogen flow line. The system is dried with a heat gun while it is flushed with dry nitrogen. The reaction vessel is then cooled in a water bath while a light positive pressure of nitrogen is maintained. The flask is charged with hydroxylamine-O-sulfonic acid (8.48 g, 0.075 mol) and 95–97% formic acid (45 mL). A solution of (5.61 g, 0.05 mol) in 15 mL of 95–97% formic acid is added with stirring over a 3-min period. After addition is complete, the reaction mixture is heated under reflux for 5 hr and then cooled to room temperature. The reaction mixture is quenched with 75 mL of ice–water. The aqueous solution is slowly neutralized to pH 7 with 6 N sodium hydroxide and extracted with three 100-mL portions of chloroform. The combined organic layers are dried with anhydrous magnesium sulfate. After removal of the solvent on a rotary evaporator, the product hexahydroazocinone is purified by distillation to give 4.6 g (72%), bp 94–96°C/0.2 mm, (short-path apparatus), lit bp 133–135°C/4 mm.
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