5-Chlorovaleryl chloride → 8-(5-chloropentanoyl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-4(2H)-one

HRID 2374565Notes

Reaction equation

HRID 2374565 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][C:8](=[O:17])[N:7]3[CH2:6]1.[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>ClCCCl>[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([C:13]1[CH:12]=[C:11]2[C:16]3=[C:15]([CH2:5][CH2:6][N:7]3[C:8](=[O:17])[CH2:9][CH2:10]2)[CH:14]=1)=[O:24]

Participants

5

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride

Product 1

HCID 111738438-(5-chloropentanoyl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-4(2H)-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Aluminum chloride (55 g, 410 mmol) was added by portions to a solution of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (30.0 g) and 5-chlorovaleryl chloride (26.8 ml) in 1,2-dichloroethane (70 ml) under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was poured into ice (500 g), extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol-diethyl ether to give a pale yellow solid (36.5 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (32.4 g) having a melting point of 110-111° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-203f9fa9bcbd4d2fbb38a6c2cb7a2eb6
Source dataset
uspto-grants-2008_12
Patent number
US07462628B2

Reaction notes

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