Reaktion #414666

Reaktionsgleichung

5-(dipropylamino)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

lithium aluminum hydride

→

1,2,5,6-tetrahydro-N,N-dipropyl-4H-pyrrolo[3,2,1-ij]quinolin-5-amine

Ausbeute 47.8%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with methanol
2. 2
   Sonstigeevaporated
3. 3
   Sonstigepartitioned between ethyl acetate and water
4. 4
   SonstigeEvaporation of the ethyl
5. 5
   Sonstigegave an oil which
6. 6
   Sonstigewas chromatographed on silica gel
7. 7
   Sonstigeto give, as the first compound
8. 8
   Wascheneluted from the column 0.27 g of 5,6-dihydro-N,N-dipropyl-4H-pyrrolo[3,2,1-ij]quinolin-5-amine (compound 87)
9. 9
   WaschenContinued elution of the column

Vorschrift

A mixture of 5-(dipropylamino)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one (0.75 g) and lithium aluminum hydride (0.21 g) was stirred in ether (20 mL) for 45 minutes. The reaction was quenched with methanol, evaporated and partitioned between ethyl acetate and water. Evaporation of the ethyl gave an oil which was chromatographed on silica gel using ethyl acetate:hexane (1:20) as eluant to give, as the first compound eluted from the column 0.27 g of 5,6-dihydro-N,N-dipropyl-4H-pyrrolo[3,2,1-ij]quinolin-5-amine (compound 87). Continued elution of the column gave 0.34 g of 1,2,5,6-tetrahydro-N,N-dipropyl-4H-pyrrolo[3,2,1-ij]quinolin-5-amine (compound 92).

Quelle