反应详情

9.5 g of 5-bromo-1-indanone and 4.93 g of CuCN are suspended in 10 ml of dimethylformamide and boiled under reflux for 4 hours. A solution of 18 g of iron(II) chloride in 5 ml of concentrated hydrochloric acid with 30 ml of water are added dropwise to the cooled, dark-brown viscous suspension while stirring, and the mixture is then stirred at 70° C. for 30 minutes. The reaction mixture is extracted by shaking three times with 50 ml of toluene, and the combined organic phases are extracted by shaking with 50 ml of 2N hydrochloric acid and 50 ml of 2N sodium hydroxide solution and then washed with water until neutral. The toluene extract is dried over magnesium sulfate and concentrated in vacuo, and the residue is recrystallized from n-heptane. 1-oxoindane-5-carbonitrile is obtained with a melting point of 123-125° C.

1. temperatureunder reflux for 4 hours
2. stirringthe mixture is then stirred at 70° C. for 30 minutes
3. extractionThe reaction mixture is extracted
4. stirringby shaking three times with 50 ml of toluene
5. extractionthe combined organic phases are extracted
6. stirringby shaking with 50 ml of 2N hydrochloric acid and 50 ml of 2N sodium hydroxide solution
7. washwashed with water until neutral
8. extractionThe toluene extract
9. dry with materialis dried over magnesium sulfate
10. concentrationconcentrated in vacuo
11. customthe residue is recrystallized from n-heptane