Sulfuric Acid → 8-Fluoro-4-methylquinoline

HRID 902016ノート

反応式

HRID 902016 の反応式
OS(O)(=O)=O.[F:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].[CH:14]([C:16]([CH3:18])=O)=[CH2:15]>O1CCOCC1>[F:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:8]=1[N:9]=[CH:15][CH:14]=[C:16]2[CH3:18]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 95842-Fluoroaniline

生成物 1

HCID 167342108-Fluoro-4-methylquinoline収率 41.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

Add H2SO4 (14.4 mL, 270 mmol) to a solution of 2-fluoroaniline (20.0 g, 180 mmol) in 1,4-dioxane (1 L) at room temperature. Heat the mixture to reflux and add methyl vinyl ketone (19.5 mL, 270 mmol) in 1,4-dioxane (50 mL) dropwise over 3 hours. Continue to heat for 1 hour after the addition, then remove the solvent under vacuum. Dissolve the residue in water (100 mL), neutralize with Na2CO3 and extract with CH2Cl2. Wash the combined organic extracts with water and brine, dry with anhydrous Na2SO4 and filter the mixture. Concentrate the filtrate; chromatograph the residue with silica gel (elute with 20% EtOAc in hexanes) to give the title compound 12 g (41%) as a yellowish solid.

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. temperatureContinue to heat for 1 hour
  4. additionafter the addition
  5. customremove the solvent under vacuum
  6. dissolutionDissolve the residue in water (100 mL)
  7. extractionextract with CH2Cl2
  8. washWash the combined organic extracts with water and brine
  9. dry with materialdry with anhydrous Na2SO4
  10. filtrationfilter the mixture
  11. concentrationConcentrate the filtrate

出典と根拠

ORDレコード
ord-a7940962a9a44cc6babb894eb7d7a0e3
出典データセット
uspto-grants-2008_04
特許番号
US07365066B2

反応ノート

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