N,N-Dimethylaniline → 6-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline

HRID 35669Notes

Reaction equation

HRID 35669 reaction equation
C1([C:4](Cl)=[O:5])CC1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12][C:11]2=[O:18].CN(C)[C:21]1[CH:26]=[CH:25]C=CC=1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:25]1[CH2:26][CH2:21]1)[C:13](=[C:4]=[O:5])[CH2:12][C:11]2=[O:18]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 77637Cyclopropanecarbonyl chlorideHCID 124791046-Chloro-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 867416286-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinolineYield 86.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

A solution of cyclopropyl-carbonyl chloride (2.09 g) in chloroform (5 ml) was added dropwise to a solution of 6-chloro-4-oxo-1,2,3,4-tetrahydroquinoline (1.815 g), N,N-dimethylaniline (2.42 g), and 4-dimethylaminopyridine (0.488 g) in chloroform (15 ml) with stirring and ice cooling over a period of 10 minutes. After being stirred overnight at ambient temperature, the mixture was washed successively with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and water, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was washed with diethyl ether and dried to give 6-chloro-1-cyclopropyl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (2.14 g).

Workup

  1. stirringAfter being stirred overnight at ambient temperature
  2. washthe mixture was washed successively with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe residual solid was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-21e8a7f3af504052bd7dac1fb7a6b25e
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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