2-Chloroaniline → 8-Chloro-2,4-dimethylquinoline

HRID 279984

반응식

HRID 279984 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10](=O)[CH:11]=[CH:12][CH3:13].[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:12]([CH3:13])[CH:11]=[C:10]2[CH3:9]

참가 물질

5

반응물 3

HCID 72402-ChloroanilineHCID 12248PentenoneHCID 14798Sodium Hydroxide

생성물 1

HCID 233230688-Chloro-2,4-dimethylquinoline수율 42%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

To 4.0 g (0.03 mol) of o-chloroaniline in 50 ml of hydrochloric acid at 100° C. was added dropwise 3.4 g (0.04 mol) of 3-penten-2-one. The mixture was refluxed for 12 hours, then neutralised with 5N sodium hydroxide and extracted with dichloromethane. The organic extract was dried and concentrated to an oil. This was purified on a silica gel column to give 2.54 g (42% of the title product; m.p. 66°-68° C. Anal. Calcd. for C11H10NCl: C, 68.94; H, 5.26; N, 7.31; Cl, 18.50. Found C, 68.87; H, 5.27; N, 7.29; Cl, 18.48.

후처리

  1. temperatureThe mixture was refluxed for 12 hours
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated to an oil
  6. customThis was purified on a silica gel column

출처 및 근거

ORD 기록
ord-d3b86189c004447b8e2d4aa0e3777bc0
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587341

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