Hydrochloric Acid → 2,4-Dimethylquinolin-8-ol

HRID 2384517노트

반응식

HRID 2384517 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl.[CH3:10][C:11](=O)[CH:12]=[CH:13][CH3:14].[OH-].[Na+]>C(OCC)(=O)C>[CH3:10][C:11]1[CH:12]=[C:13]([CH3:14])[C:7]2[C:2](=[C:3]([OH:8])[CH:4]=[CH:5][CH:6]=2)[N:1]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 58012-AminophenolHCID 12248PentenoneHCID 14798Sodium Hydroxide

생성물 1

HCID 206416412,4-Dimethylquinolin-8-ol수율 36.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

In a three-necked flask were placed 33 g of o-aminophenol and 207 g of concentrated hydrochloric acid and the mixture was heated to the reflux temperature and stirred for 1 hour. To the mixture being heated under reflux was slowly added 51 g of 3-penten-2-one with a purity of 65% over 2 hours and stirring was continued for another 2 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, 300 ml of a 48% aqueous solution of NaOH was added until the aqueous phase became alkaline. Ethyl acetate was added further, the organic layer was recovered and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by gas chromatography, recrystallized from hexane and the crystals collected by filtration were washed with hexane and dried at 80° C. under reduced pressure to give 18.9 g of 2,4-dimethyl-8-quinolinol.

후처리

  1. customIn a three-necked flask were placed
  2. temperatureTo the mixture being heated
  3. temperatureunder reflux
  4. customover 2 hours
  5. stirringstirring
  6. waitwas continued for another 2 hours
  7. customUpon completion of the reaction
  8. customthe organic layer was recovered
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe crude product thus obtained
  11. customwas purified by gas chromatography
  12. customrecrystallized from hexane
  13. filtrationthe crystals collected by filtration
  14. washwere washed with hexane
  15. customdried at 80° C. under reduced pressure

출처 및 근거

ORD 기록
ord-8d2058bba76445a985888607fbdf5131
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263770B2

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