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

HRID 40431

反応式

HRID 40431 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-457694425c8b4e2bb48d37dcff1b7b13
出典データセット
uspto-grants-2013_09
特許番号
US08530059B2

関連ノート

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