反应详情

Ethyl 1-aminocyclopropanecarboxylate hydrochloride (16 g) in chloroform (50 ml) was added to 1,2-bis(bromomethyl)naphthalene (40 g) and potassium carbonate (40 g) in chloroform (200 ml) kept at 60°. The reaction mixture was refluxed for a further 6 hr and then filtered; the filtrate was evaporated to dryness and the residue [i.e. crude 2-(1'-carbethoxycyclopropyl)benz[e]isoindoline] was dissolved in THF (150 ml) and added to lithium aluminium hydride (10 g) in THF (100 ml) over 0.5 h. Water was then added and the resultant slurry was filtered and the filtrate was evaporated to dryness; the residue was partitioned between ether and water and the ether layer was extracted with concentrated hydrochloric acid. The acidic extract was evaporated to dryness to give a residue which was recrystallised from iso-propanol/ethyl acetate to give the title compound (5.9 g. m.p.192°).

1. customkept at 60°
2. temperatureThe reaction mixture was refluxed for a further 6 hr
3. filtrationfiltered
4. customthe filtrate was evaporated to dryness
5. dissolutionthe residue [i.e. crude 2-(1'-carbethoxycyclopropyl)benz[e]isoindoline] was dissolved in THF (150 ml)
6. additionadded to lithium aluminium hydride (10 g) in THF (100 ml) over 0.5 h
7. additionWater was then added
8. filtrationthe resultant slurry was filtered
9. customthe filtrate was evaporated to dryness
10. customthe residue was partitioned between ether and water
11. extractionthe ether layer was extracted with concentrated hydrochloric acid
12. extractionThe acidic extract
13. customwas evaporated to dryness
14. customto give a residue which
15. customwas recrystallised from iso-propanol/ethyl acetate