تفاعل #527030

معادلة التفاعل

hydrochloric acid

5,10-dihydro-8-methoxy-6-methylindeno[1,2-b]indole

morpholino borane

hydrochloric acid

water

→

title compound

المردود 38.4%

cis-4b,5,9b,10-Tetrahydro-8-methoxy-6-methylindeno[1,2-b]indole

المردود 38.4%

المذيبات

tetrahydrofurane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture stirred over night
2. 2
   أخرىthe mixture evaporated
3. 3
   درجة الحرارة5 ml of conc. hydrochloric acid and the mixture was heated on a water bath until most of the solid material
4. 4
   workup.DISSOLUTIONhad dissolved
5. 5
   ترشيحThe solution was then filtered hot
6. 6
   درجة الحرارةthe filtrate cooled
7. 7
   workup.ADDITIONalkalinized by addition of 10M sodium hydroxide solution
8. 8
   ترشيحFiltration
9. 9
   غسيلwashing with water

الإجراء التجريبي

To a solution of 5.0 g (0.020 mol) of 5,10-dihydro-8-methoxy-6-methylindeno[1,2-b]indole in 50 ml of tetrahydrofurane was added 8.1 g (0.080 mol) of morpholino borane and dropwise 6.3 ml of conc. hydrochloric acid. The initially exothermic reaction mixture was stirred at room temperature for 72 hour. An additional 6.3 ml of conc. hydrochloric acid was then added and the mixture stirred over night. 25 ml of water was then added and the mixture evaporated. The residue was suspended in 200 ml of water and 5 ml of conc. hydrochloric acid and the mixture was heated on a water bath until most of the solid material had dissolved. The solution was then filtered hot and the filtrate cooled and alkalinized by addition of 10M sodium hydroxide solution. Filtration and washing with water gave 1.93 g (38.4%) of the title compound 1H NMR (CDCl3) δ: 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