Реакция #54504

Уравнение реакции

sulfuric acid

product

5ξ-hydroxy-7-amino-6,7,8,9-tetrahydro [5 H] benzocycloheptene

dioxane

→

7-amino-6,7-dihydro [5H] benzocycloheptene

Выход 59.6%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураthe mixture was refluxed for 2 hours
2. 2
   Экстракцияthe neutral fraction was extracted with ether
3. 3
   workup.ADDITIONwith sodium hydroxide addition
4. 4
   Экстракцияwas extracted with ethyl acetate
5. 5
   ПромывкаThe ethyl acetate extracts were washed with aqueous sodium chloride solution
6. 6
   Другоеdried
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated to dryness
9. 9
   Другоеto obtain 5 g of raw product
10. 10
    ДругоеThe latter was chromatographed over silica gel
11. 11
    Промывкаwas eluted with an 8-2-1 ethyl acetate-benzene-triethylamine mixture

Методика

12 ml of 18N sulfuric acid were added to a refluxing mixture of 5.6 g of the product of Step C and 60 ml of dioxane and the mixture was refluxed for 2 hours and then was cooled to 20° C. The mixture was poured into 300 ml of water and the neutral fraction was extracted with ether. The aqueous phase was made alkaline with sodium hydroxide addition and was extracted with ethyl acetate. The ethyl acetate extracts were washed with aqueous sodium chloride solution, dried, filtered and evaporated to dryness to obtain 5 g of raw product. The latter was chromatographed over silica gel and was eluted with an 8-2-1 ethyl acetate-benzene-triethylamine mixture to obtain 3 g of 7-amino-6,7-dihydro [5H] benzocycloheptene in the form of a brown oil.

Источник