反应详情

温度

80 °C

To a solution of 6.17 g. (26.25 mmoles) of 1-methyl-7-benzoylindole in 62 ml. of methylene chloride was added 3.58 g. (26.25 mmoles) of 98% N-chlorosuccinimide and the mixture allowed to stir for 90 minutes. An additional 720 mg. of N-chlorosuccinimide was added and stirring continued for 2 hours. The reaction mixture was concentrated in vacuo and 52 ml. of acetic acid added. The mixture was heated to 80° C. and 27 ml. of 85% phosphoric acid was added. The temperature was raised to reflux for 90 minutes and the reaction was cooled and poured into 200 ml. of ice and water. The precipitate was filtered, dissolved in methylene chloride and the solution dried with magnesium sulfate. Removal of the solvent gave a residue which was dissolved in 5% diethyl ether-methylene chloride and filtered through silica gel. The fractions were collected, combined and concentrated to give 4.0 g. of the product as a viscous oil.

1. stirringstirring
2. waitcontinued for 2 hours
3. concentrationThe reaction mixture was concentrated in vacuo and 52 ml
4. additionof acetic acid added
5. additionof 85% phosphoric acid was added
6. temperatureThe temperature was raised
7. temperatureto reflux for 90 minutes
8. temperaturethe reaction was cooled
9. additionpoured into 200 ml
10. filtrationThe precipitate was filtered
11. dissolutiondissolved in methylene chloride
12. dry with materialthe solution dried with magnesium sulfate
13. customRemoval of the solvent
14. customgave a residue which
15. filtrationfiltered through silica gel
16. customThe fractions were collected
17. concentrationconcentrated
18. customto give 4.0 g