反应详情

Fuming nitric acid (40 ml, 1.5 g/ml) was added dropwise with stirring to acetic anhydride (80 ml ) keeping the temperature of the mixture at 0° C. After the addition was complete 2-cyanoindane (11.33 g, 79.5 mmol), (J. Chem. Soc. (B), (1969), 1197) was added dropwise with stirring over 30 minutes maintaining the reaction temperature between -5° and 0° C. The mixture was stirred for a further 15 minutes then poured onto ice. The mixture was extracted with dichloromethane (4×150 ml) and the extracts were washed with saturated aqueous sodium bicarbonate (3×150 ml), dried over magnesium sulphate and the solvent evaporated under reduced pressure. The residue was recrystallised from ethanol to give 2-cyano-5-nitroindane (12.09 g, 81%) as a yellow solid, m.p. 80°-82° C.

1. customat 0° C
2. additionAfter the addition
3. additionwas added dropwise
4. temperaturemaintaining the reaction temperature between -5° and 0° C
5. stirringThe mixture was stirred for a further 15 minutes
6. additionthen poured onto ice
7. extractionThe mixture was extracted with dichloromethane (4×150 ml)
8. washthe extracts were washed with saturated aqueous sodium bicarbonate (3×150 ml)
9. dry with materialdried over magnesium sulphate
10. customthe solvent evaporated under reduced pressure
11. customThe residue was recrystallised from ethanol