Hydrochloric Acid → 8-Fluoro-4-methylquinoline

HRID 131630ノート

反応式

HRID 131630 の反応式
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[CH:10]([C:12]([CH3:14])=O)=[CH2:11]>C(O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:11][CH:10]=[C:12]2[CH3:14]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 95842-Fluoroaniline

生成物 1

HCID 167342108-Fluoro-4-methylquinoline

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 16211236Trichloroiron;hexahydrate触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-fluoroaniline (25 ml) in ethanol (185 ml) was added concentrated hydrochloric acid (21 ml), iron (III) chloride hexahydrate (111 g) and zinc (II) chloride (4.1 g) and the resulting mixture was heated to 60° C. Methyl vinyl ketone (25 ml) was added dropwise over 45 min. then the mixture was refluxed for 2 hrs. The reaction mixture was allowed to cool then evaporated under reduced pressure. The resulting oil was basified to pH 12 with 2M sodium hydroxide solution, filtered through arbocel and then the aqueous was extracted with ethyl acetate (×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with i-hexane/diethyl ether (3:1) followed by i-hexane/diethyl ether (2:1) to give the sub-title compound as a solid (8.25 g).

後処理

  1. temperaturethe mixture was refluxed for 2 hrs
  2. temperatureto cool
  3. customthen evaporated under reduced pressure
  4. filtrationfiltered through arbocel
  5. extractionthe aqueous was extracted with ethyl acetate (×2)
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with i-hexane/diethyl ether (3:1)

出典と根拠

ORDレコード
ord-34942b22469847ef93fc4322a781827e
出典データセット
uspto-grants-2008_06
特許番号
US07384951B2

反応ノート

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