Water → 1-(4-chlorophenyl)-8,9-dihydro-7-methylene-7H-pyrrolo[3,2,1-ij]quinoline

HRID 263426Notes

Reaction equation

HRID 263426 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:24]3=[C:25]4[C:20]([C:21](=O)[CH2:22][CH2:23]3)=[CH:19][CH:18]=[CH:17][N:16]4[CH:15]=2)=[CH:10][CH:9]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:24]3=[C:25]4[C:20]([C:21](=[CH2:1])[CH2:22][CH2:23]3)=[CH:19][CH:18]=[CH:17][N:16]4[CH:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 190380211-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin-7-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 190380201-(4-chlorophenyl)-8,9-dihydro-7-methylene-7H-pyrrolo[3,2,1-ij]quinoline

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

Methyltriphenylphosphonium bromide (3.8 g) was added to 25 ml of anhydrous tetrahydrofuran. To this mixture was added the solution of potassium t-butoxide (1.2 g) in 25 ml of tetrahydrofuran at ambient temperature. After stirring for 3 hours, to this solution was added the solution of 1-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin-7-one (1.5 g), which was obtained in example 2, in 15 ml of tetrahydrofuran. After stirring for 30 min., to this solution was added water and extracted with ethyl acetate. The organic solution was washed with brine and dried over anhydrous sodium sulfate. After removing drying agent by filtration and organic solvent by evaporation under reduced pressure, the residue was purified by alumina column chromatography, and the title compound was obtained as yellow crystals (1.1 g) .

Workup

  1. stirringAfter stirring for 30 min., to this solution
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing
  6. customdrying agent
  7. filtrationby filtration and organic solvent
  8. customby evaporation under reduced pressure
  9. customthe residue was purified by alumina column chromatography

Sources & evidence

ORD record
ord-35a96525160248209cc22e79df0949ea
Source dataset
uspto-grants-1997_07
Patent number
US05643920

Reaction notes

Loading…