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

HRID 279984

反応式

HRID 279984 の反応式
[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]

参加物

5

反応物 3

HCID 72402-ChloroanilineHCID 12248PentenoneHCID 14798Sodium Hydroxide

生成物 1

HCID 233230688-Chloro-2,4-dimethylquinoline収率 42%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3b86189c004447b8e2d4aa0e3777bc0
出典データセット
uspto-grants-1986_05
特許番号
US04587341

関連ノート

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