تفاعل #527031

معادلة التفاعل

hydrochloric acid

sodium hydroxide

5,10-dihydro-8-methoxy-7,9-dimethylindeno[1,2-b]indole

morpholino borane

hydrochloric acid

→

title compound

cis-4b,5,9b,10-Tetrahydro-8-methoxy-7,9-dimethylindeno[1.2-b]indole

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 30 minutes
2. 2
   workup.ADDITIONwas added
3. 3
   درجة الحرارةThe resulting mixture was then refluxed for 15 minutes
4. 4
   درجة الحرارةAfter cooling the solution
5. 5
   استخلاصextracted three times with ether
6. 6
   أخرىDrying
7. 7
   أخرى(MgSO4) and evaporation
8. 8
   أخرىgave a crude product, which
9. 9
   أخرىwas crystallized
10. 10
    workup.DISSOLUTIONby dissolving in ethyl acetate
11. 11
    workup.ADDITIONaddition of light petroleum at -20° C
12. 12
    ترشيحFiltration

الإجراء التجريبي

To an solution of 0.8 g (0.3 mmol) of 5,10-dihydro-8-methoxy-7,9-dimethylindeno[1,2-b]indole and 1,21 g of morpholino borane in 4 ml of dioxane was added dropwise 1 ml of conc. hydrochloric acid. The mixture was refluxed for 30 minutes, then cooled whereupon 3 ml of 6M hydrochloric acid was added. The resulting mixture was then refluxed for 15 minutes. After cooling the solution was alkalinized with aqueous sodium hydroxide and extracted three times with ether. Drying (MgSO4) and evaporation gave a crude product, which was crystallized by dissolving in ethyl acetate and addition of light petroleum at -20° C. Filtration gave 0.73 g (92%) of the title compound. 1H NMR(CDCl3) 2.08 (3H,s), 3.15-3.25 (1H,dd), 3,42-3,55 (1H,dd), 3.7 (3H,s), 4.1-4.22 (1H,t) 5.22-5.28 (1H,d), 6.42-6.46 (1H,d), 6.6- 6.65 (1H,d) 7.14-7.25 (3H,m), 7.3-7.4 (1H,m).

المصدر