2-Fluoroaniline → HCID 178527297、化合物

HRID 72640

反応式

HRID 72640 の反応式
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]1([S:15]([C:18](=[CH:23]OCC)[C:19](OC)=[O:20])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C2C=CC=CC=2)C=CC=CC=1.CCOCC>[OH:20][C:19]1[C:5]2[C:3](=[C:2]([F:1])[CH:8]=[CH:7][CH:6]=2)[N:4]=[CH:23][C:18]=1[S:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:17])=[O:16]

参加物

4

反応物 2

HCID 95842-FluoroanilineHCID 86698553Methyl 2-phenylsulfonyl-3-ethoxy-acrylate

生成物 1

HCID 178527297HCID 178527297、化合物収率 3.3%

試薬・触媒・溶媒 1

HCID 665887421,1'-Biphenyl;ethoxyethane溶媒

反応条件

温度
260 °C

実験手順

2-Fluoroaniline 7(1) (3.82 g, 0.0344 mol) and methyl 2-phenylsulfonyl-3-ethoxy-acrylate 7(2) (9.59 g, 0.0355 mol) were mixed together in biphenyl ether (21.5 ml). The mixture was stirred in an opened flask for 6 h at 250-270° C. Ethanol was distilled during the first 30 min. After the reaction was completed (LCMS control) the mixture was cooled, the formed solid was filtered off, dissolved in ethanol and solution was boiled with charcoal. After filtration from charcoal ethanol was evaporated, the residue was subjected to chromatography on silica, eluent—gradient of solvent system CHCl3:ethyl acetate=from 10:1 to 5:1. The residue after evaporation of fractions, comprising the final product was washed with ether, it gave 345 mg (3.3%) of 4-hydroxy-3-phenylsulfonyl-8-fluoroquinoline 7(3).

後処理

  1. distillationEthanol was distilled during the first 30 min
  2. temperaturewas cooled
  3. filtrationthe formed solid was filtered off
  4. dissolutiondissolved in ethanol
  5. filtrationAfter filtration from charcoal ethanol
  6. customwas evaporated
  7. customThe residue after evaporation of fractions
  8. washwas washed with ether, it

出典と根拠

ORDレコード
ord-b01098ec6aa14f9286d6937892b971e1
出典データセット
uspto-grants-2014_09
特許番号
US08829002B2

関連ノート

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