反应详情

Potassium hydroxide (9.0 g) was added to a solution of 2-(n-undecyl)indole-6-carboxylic acid (22.1 g) in dimethylsulphoxide (100 ml) and water (5 ml), and the mixture was stirred and warmed on a steam bath to give a suspension. After 15 minutes the suspension was removed from the steam bath, methyl iodide (15 ml) was added, and the mixture was stirred for 2 hours with occasional warming. Methyl iodide (10 ml) was added and the mixture was stirred for 1 hour. The mixture was left to cool overnight and was then poured into water and acidified with 2N hydrochloric acid. The product was collected and washed. This product was then added to a mixture of ethanol (150 ml), water (50 ml), and sodium hydroxide (6.5 g), and the mixture was heated under reflux for 1 hour and then poured into water containing acetic acid (50 ml). The product was twice recrystallised from ethanol to give 1-methyl-2-(n-undecyl)indole-6-carboxylic acid (9.6 g), in the form of a white powder, m.p. 165°-168° C.

1. temperaturewarmed on a steam bath
2. customto give a suspension
3. customAfter 15 minutes the suspension was removed from the steam bath, methyl iodide (15 ml)
4. additionwas added
5. stirringthe mixture was stirred for 2 hours with occasional warming
6. additionMethyl iodide (10 ml) was added
7. stirringthe mixture was stirred for 1 hour
8. waitThe mixture was left
9. temperatureto cool overnight
10. additionwas then poured into water
11. customThe product was collected
12. washwashed
13. additionThis product was then added to a mixture of ethanol (150 ml), water (50 ml), and sodium hydroxide (6.5 g)
14. temperaturethe mixture was heated
15. temperatureunder reflux for 1 hour
16. additionpoured into water
17. additioncontaining acetic acid (50 ml)
18. customThe product was twice recrystallised from ethanol