Pyridine → 7-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone

HRID 1073062

반응식

HRID 1073062 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O1CCOCC1.[CH3:25][N:26]([CH3:36])[C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>ClCCl.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][N:9]2[C:29](=[O:30])[C:28]2[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=2[N:26]([CH3:25])[CH3:36])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 889747-Chloro-2,3-dihydro-4-quinoloneHCID 221579792-(Dimethylamino)benzoyl chloride

생성물 1

HCID 231668547-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone수율 96.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 7-chloro-2,3-dihydro-4(lH)-quinolinone (20 g), pyridine (26 g) and dioxane (200 ml) was added dropwise 2-dimethylaminobenzoyl chloride (30 g) under cooling at 0° C. to 5° C. with stirring. The mixture was allowed to react at room temperature for additional 3 hours. The reaction mixture was poured into 500 ml of water, then shaken with additional dichloromethane (1000 ml). The organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each) then once with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. Dichloromethane was removed in vacuo and the residue was recrystallized with dichloromethane and n-hexane to obtain 7-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone (yield 35 g) as white crystal.

후처리

  1. temperatureunder cooling at 0° C. to 5° C.
  2. customto react at room temperature for additional 3 hours
  3. washThe organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each)
  4. dry with materialonce with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  5. customDichloromethane was removed in vacuo
  6. customthe residue was recrystallized with dichloromethane and n-hexane

출처 및 근거

ORD 기록
ord-2aee0c3fa5394b8281ce63ebaae96816
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968680

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