Potassium Carbonate → N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide

HRID 1603087노트

반응식

HRID 1603087 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:17]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O.O>[C:17]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[O:31])=[CH:33][CH:34]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 125009584-Benzoylaminobenzoyl chloride

생성물 1

HCID 10642000N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide수율 74.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매2회

실험 절차

To a solution of 1,2,3,4-tetrahydroquinoline (28.7 g) in acetone (400 ml) and water (200 ml) is added potassium carbonate (38.8 g) and further thereto is added 4-benzoylaminobenzoyl chloride (56 g) under ice-cooling. The mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the mixture is extracted with dichloromethane. The extract is dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography and recrystallized from methanol to give 1-[4-(benzoylamino)benzoyl-]-1,2,3,4-tetrahydroquinoline (57 g) as white powder, m.p. 202.5-203.5° C.

후처리

  1. temperaturecooling
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography
  6. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-5416b3f320964db99496e17142cb5cd2
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05985869

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