Dichloromethane → HCID 12404423, compound

Participants

Reaction Steps

To a slurry of 53.2 g (0.4 mol) of aluminum chloride in 80 mL of diclorobenzene was added portionwise 38.0 g (0.2 mol) of N-acetylisonipecotic acid chloride (by closed addition method) so as to maintain at 5°-10°. During the addition a total of 50 mL of methylene chloride was added as needed. After the addition was complete the mixture was allowed to come to room temperature and stirred for two days. The mixture was poured onto an excess of crushed ice. The aqueous mixture was extracted several times with chloroform. The collected extracts were dried over anhydrous sodium sulfate and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was triturated in isopropyl ether. The residue crystallized and 22 g (36.5%) of crude product was obtained. A 5-g sample was recrystallized from acetone-water after treatment with charcoal. After air-drying the off-white solid was recrystallized from isopropyl ether-methanol, mp 134°-136°.

Provenance & Evidence