反应详情

Thionyl chloride (34.8 ml, 480 mmol) was added to a mixture of 2-(1,3-dioxo-2-azaindan-2-yl)-4-methylpentanoic acid (83.61 g, 320 mmol) and benzene (320 ml). The resulting mixture was heated under reflux for 2 hours. The solvent and excess thionyl chloride were removed by distillation under reduced pressure, followed by addition of benzene (320 ml). The benzene was removed and fresh benzene (480 ml) was added to form a solution. Anhydrous aluminum chloride (106.7 g, 800 mmol) was added immediately to the solution and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice-water (700 ml). The aqueous layer was extracted with benzene (200 ml). After being washed first with water and then with an aqueous sodium bicarbonate solution and with brine, the combined organic layer was dried over sodium sulfate and then evaporated under reduced pressure. The residue was treated with ethanol to give crystals. The crystals were dissolved with heating in ethanol (80 ml) and hexane (160 ml) was added. Precipitated crystals were collected by filtration and washed first with a 1:2 mixed solution (240 ml) of ethanol and hexane and then with hexane. The crystals were dried in air to obtain 74.6 g of the title compound as white crystals (yield: 73%).

1. temperatureThe resulting mixture was heated
2. temperatureunder reflux for 2 hours
3. customThe solvent and excess thionyl chloride were removed by distillation under reduced pressure
4. additionfollowed by addition of benzene (320 ml)
5. customThe benzene was removed
6. additionfresh benzene (480 ml) was added
7. customto form a solution
8. extractionThe aqueous layer was extracted with benzene (200 ml)
9. washAfter being washed first with water
10. dry with materialwith an aqueous sodium bicarbonate solution and with brine, the combined organic layer was dried over sodium sulfate
11. customevaporated under reduced pressure
12. additionThe residue was treated with ethanol
13. customto give crystals
14. dissolutionThe crystals were dissolved
15. customPrecipitated crystals
16. filtrationwere collected by filtration
17. washwashed first with a 1:2 mixed solution (240 ml) of ethanol and hexane
18. customThe crystals were dried in air