反应详情

A 3-liter, three-necked flask equipped with a dry ice condenser, mechanical stirrer and Claisen adapter fitted with an ammonia gas inlet and nitrogen inlet is rinsed with acetone, dried in an oven at 125° C., and heated with an air gun while flushing with nitrogen. The apparatus is cooled in a dry ice-acetone bath and the condenser is filled with a dry ice-acetone mixture. Ammonia gas flow is initiated and 600 ml is condensed out. The ammonia inlet tube is replaced by a stopper, and 0.4 g of powdered iron (III) nitrate is added. Sodium metal, 51.52 g (2.24 moles) is added in small portions over 1 hour. After all the sodium is added, the dry ice bath is removed and cooling is left to the dry ice condenser. Complete conversion of the sodium/ammonia solution to sodamide is indicated by a color change from deep blue to gray. Next, 92.82 g (0.56 mole) of 3-(o-chlorophenyl)propionitrile is added over a period of 10 minutes. The last traces of the nitrile are washed into the flask with small amounts of anhydrous ethyl ether. The dark green reaction mixture is stirred vigorously for 3 hours and then is treated with 134.4 g (1.68 moles) of solid ammonium nitrate. The ammonia is allowed to evaporate overnight at room temperature. Water (420 ml) is cautiously added to the residue. The organic layer is taken up in two 224-ml portions of chloroform, and the solutions are combined and washed twice with 140 ml of aqueous 5 percent hydrochloric acid and once with 140 ml of water. The chloroform solution is dried over anhydrous magnesium sulfate, filtered, and evaporated on a rotary evaporator. The residual liquid is distilled under reduced pressure through an insulated 12-inch Vigreux column. The product is collected at 59° C.-69° C./0.2 mm Hg. The infrared, 'H and 13C nuclear magnetic resonance are run to identify the product. The yield is 50 percent.

1. customA 3-liter, three-necked flask equipped with a dry ice condenser, mechanical stirrer
2. customClaisen adapter fitted with an ammonia gas inlet and nitrogen inlet
3. washis rinsed with acetone
4. customdried in an oven at 125° C.
5. temperatureheated with an air gun
6. customwhile flushing with nitrogen
7. temperatureThe apparatus is cooled in a dry ice-acetone bath
8. additionthe condenser is filled with a dry ice-acetone mixture
9. customcondensed out
10. additionis added
11. customthe dry ice bath is removed
12. temperaturecooling
13. waitis left to the dry ice condenser
14. washThe last traces of the nitrile are washed into the flask with small amounts of anhydrous ethyl ether
15. customto evaporate overnight at room temperature
16. additionWater (420 ml) is cautiously added to the residue
17. washwashed twice with 140 ml of aqueous 5 percent hydrochloric acid and once with 140 ml of water
18. dry with materialThe chloroform solution is dried over anhydrous magnesium sulfate
19. filtrationfiltered
20. customevaporated on a rotary evaporator
21. distillationThe residual liquid is distilled under reduced pressure through an insulated 12-inch Vigreux column
22. customThe product is collected at 59° C.-69° C./0.2 mm Hg