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

HRID 745053

반응식

HRID 745053 반응식
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>ClCCl>[C:27]([NH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

생성물 1

HCID 10642000N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide수율 34.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (0.5 g) in dichloromethane (20 ml) is added triethylamine (0.3 g), and thereto is added benzoyl chloride (0.28 g) under ice-cooling. The mixture is stirred at room temperature for 1 hour. To the reaction mixture is added water and 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 (eluent; dichloromethane:methanol=50:1) and recrystallized from methanol to give 1-[4-(benzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (245 mg) as white powder, m.p. 202.5°-203.5° C.

후처리

  1. temperaturecooling
  2. extractionextracted 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 (eluent; dichloromethane:methanol=50:1)
  6. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-608d591068fe4b3b940f9b1ad53add91
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559230

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