Sulfuric Acid → 8-Fluoro-4-methylquinoline

HRID 902016노트

반응식

HRID 902016 반응식
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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 95842-Fluoroaniline

생성물 1

HCID 167342108-Fluoro-4-methylquinoline수율 41.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7940962a9a44cc6babb894eb7d7a0e3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365066B2

반응 노트

불러오는 중…