Hydrocarbostyril → 2(1H)-Quinolinone, 6-(2-chloro-1-oxopropyl)-3,4-dihydro-

HRID 1458785Notes

Reaction equation

HRID 1458785 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH:6]([CH3:10])[C:7](Cl)=[O:8].[NH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:21]>C(=S)=S>[Cl:5][CH:6]([CH3:10])[C:7]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[NH:11][C:12](=[O:21])[CH2:13][CH2:14]2)=[O:8]

Participants

5

Reactant 3

HCID 64796HydrocarbostyrilHCID 1110192-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 131049192(1H)-Quinolinone, 6-(2-chloro-1-oxopropyl)-3,4-dihydro-

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

Aluminum chloride (109 g, 817 mmol) was slurried in carbon disulfide (600 mL) and 2-chloropropionyl chloride (16.8 mL, 173.07 mmol) was added. To this mixture was added 3,4-dihydro-2(1H)-quinolone (20.0 g, 135.89 mmol, J. Amer. Chem. Soc., 1944, 66, 1442). The mixture was refluxed for 4 hours, cooled, and the carbon disulfide poured off and discarded. The reddish residue was carefully quenched with ice water which caused the product to solidify. The solids were collected, rinsed well with water, and suctioned dry followed by drying in vacuo. The product weighed 31.37 g (97%) and had mp 205°-206° C. Analysis calculated for C12H12CINO2 : C, 60.64; H, 5.09; N, 5.89. Found: C, 60.20; H, 4.89; N, 5.78.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturecooled
  3. customThe reddish residue was carefully quenched with ice water which
  4. customThe solids were collected
  5. washrinsed well with water
  6. customsuctioned dry
  7. customby drying in vacuo

Sources & evidence

ORD record
ord-706508bf7a944230b5efe3e24e0e08a7
Source dataset
uspto-grants-1998_12
Patent number
US05852040

Reaction notes

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