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

HRID 653119Notes

Reaction equation

HRID 653119 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-e478162fa4754bcf9267e7a1f02e53a1
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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