Sodium Hydroxide → (2-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone

HRID 463030노트

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HRID 463030 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5].Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]([C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[NH:1][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:5]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 761652-Amino-2'-chlorobenzophenoneHCID 796132-Chloro-3-nitropyridine

생성물 1

HCID 13388386(2-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone수율 38.3%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

Under nitrogen atmosphere, 44.4 g (0.192 mole) of 2-amino-2'-chlorobenzophenone was added in four portions at 15 min intervals to a stirred melt (130°-135° C.) of 33.5 g (0.211 mole) of 2-chloro-3-nitropyridine. Heating was continued for 30 min at 130°-125° C. and for 45 min at 145° C. The reaction mixture was cooled to 110° C. and 200 ml of hot toluene was added. To the cooled mixture (room temperature) 100 ml of 10% aqueous sodium hydroxide was added and stirring was continued for 15 min. The toluene layer was separated and washed three times with 75 ml portions of water, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in 300 ml of methylene chloride and the solution was stirred with 100 g of fluorisil for 30 min. The mixture was filtered, rinsing the fluorisil filter-cake several times with methylene chloride. The combined filtrates were treated in the same manner with an additional 100 g of fluorisil. The methylene chloride was separated by filtration and concentrated in vacuo. The residue was crystallized from ethyl acetate-cyclohexane to give 26.0 g of a bright yellow solid, m.p. 119° C. A second crop (7.0 g) was obtained from the filtrate and recrystallized from isopropyl ether, m.p. 118°-119° C. The total yield amounted to 49% of theory.

후처리

  1. temperatureHeating
  2. waitwas continued for 15 min
  3. customThe toluene layer was separated
  4. washwashed three times with 75 ml portions of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in 300 ml of methylene chloride
  8. stirringthe solution was stirred with 100 g of fluorisil for 30 min
  9. filtrationThe mixture was filtered
  10. washrinsing the fluorisil
  11. filtrationfilter-cake several times with methylene chloride
  12. additionThe combined filtrates were treated in the same manner with an additional 100 g of fluorisil
  13. customThe methylene chloride was separated by filtration
  14. concentrationconcentrated in vacuo
  15. customThe residue was crystallized from ethyl acetate-cyclohexane

출처 및 근거

ORD 기록
ord-c0cf241de098438e8f80ccafc6afe97d
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04518603

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