HCID 11311820, compound → HCID 11149594, compound

HRID 327484Notes

Reaction equation

HRID 327484 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8]3=[C:9]([CH2:15][C:16](=O)[N:7]3[CH2:6]1)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][C:13]2[C:8]3=[C:9]([CH2:15][CH2:16][N:7]3[CH2:6]1)[CH:10]=[CH:11][CH:12]=2)[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 11311820HCID 11311820, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11149594HCID 11149594, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  1. customThe reaction was quenched with methanol
  2. customevaporated
  3. custompartitioned between ethyl acetate and water
  4. customEvaporation of the ethyl
  5. customgave an oil which
  6. customwas chromatographed on silica gel
  7. customto give, as the first compound
  8. washeluted 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. washContinued elution of the column

Sources & evidence

ORD record
ord-ae95935ebcc842abb8cb052c971d2593
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…