Acrolein → 3-Chloro-7,8-dihydroquinolin-5(6H)-one

HRID 1591252Notes

Reaction equation

HRID 1591252 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8](=[CH:11]Cl)[CH:9]=O.[NH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1.C(C=C)=O>C(Cl)Cl.CN(C)C=O>[Cl:7][C:8]1[CH:9]=[N:13][C:14]2[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[C:15]=2[CH:11]=1

Participants

7

Reactant 4

HCID 7847AcroleinHCID 65578Oxalyl chlorideHCID 1505162,3-Dichloro-2-propenalHCID 218731843-Aminocyclohexan-1-one

Product 1

HCID 109976543-Chloro-7,8-dihydroquinolin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

In reaction 3 of Scheme 1, a solution of oxalyl chloride in methylene chloride is added dropwise to a solution of chloromalondialdehyde III in methyene chloride and a phase transfer catalyst, such as dimethylformamide, under inert reaction conditions. The reaction mixture is stirred at room temperature until conversion to the corresponding 2,3-dichloroacrolein is complete. In reaction 4 of Scheme 1, a solution of 1-amino-cyclohexan-3-one VI in dimethylformamide is added dropwise to the above acrolein to form the corresponding 3-chloro-5,6,7,8-tetrahydroquinolin-5-one VII. The reaction, generally carried out overnight, will be in the temperature range between about 60° C. to about 80° C., preferably about 70° C.

Workup

  1. customIn reaction 3 of Scheme 1
  2. customIn reaction 4 of Scheme 1

Sources & evidence

ORD record
ord-4de99e44c85c41d488652a206de3a760
Source dataset
uspto-grants-1993_04
Patent number
US05206367

Reaction notes

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