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

HRID 653119노트

반응식

HRID 653119 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e478162fa4754bcf9267e7a1f02e53a1
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675324

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