Potassium Carbonate → 2-(3-Methylphenyl)-6-methoxyquinoline

HRID 40431

반응식

HRID 40431 반응식
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:9][C:5]1[CH:4]=[C:3]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[N:14]=2)[CH:8]=[CH:7][CH:6]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 836472-Chloro-6-methoxyquinolineHCID 866123723-Methylphenyl borate

생성물 1

HCID 588711762-(3-Methylphenyl)-6-methoxyquinoline

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

3-Methylphenyl borate (1.3 mmol), 2-chloro-6-methoxyquinoline (1 mmol), tetrakis(triphenylphosphine) palladium(O) (0.05 mmol) and potassium carbonate (3 mmol) were dissolved in THF (30 mL) and H2O (10 mL). The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the solvents were removed. The reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 2-(3-methylphenyl)-6-methoxyquinoline as a solid.

후처리

  1. customAfter completion of the reaction
  2. customthe solvents were removed
  3. extractionThe reaction mixture was extracted with dichloromethane and water
  4. distillationdistilled under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography
  6. distillationThe eluate was distilled under reduced pressure
  7. customThe residue was recrystallized from dichloromethane and petroleum ether
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-457694425c8b4e2bb48d37dcff1b7b13
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530059B2

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