4-Chloro-2-methylquinoline → (3-(2-Dimethylamino-ethoxy)-4-methyl-phenyl)-(2-methyl-quinolin-4-yl)-amine

HRID 914964

反応式

HRID 914964 の反応式
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:26])[CH:17]=1>CCO.Cl>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:9][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]([CH3:26])[CH:17]=2)[CH:10]=[CH:11][C:12]=1[CH3:13]

参加物

5

反応物 2

HCID 779734-Chloro-2-methylquinolineHCID 392392273-(2-Dimethylamino-ethoxy)-4-methylaniline

生成物 1

HCID 58958140(3-(2-Dimethylamino-ethoxy)-4-methyl-phenyl)-(2-methyl-quinolin-4-yl)-amine収率 57.8%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 702Ethanol溶媒

実験手順

To a solution of 9 (0.25 g, 1.29 mmol) and 5 (0.29 ml, 1.44 mmol) in EtOH (8 mL) were added 2 drops of conc. HCl. The mixture was heated under reflux overnight. After cooling to room temperature, EtOH was removed under reduced pressure. The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) and the aquous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, the solids were filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc) to yield the title compound as a light yellow solid (0.25 g).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customEtOH was removed under reduced pressure
  4. customThe residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each)
  5. extractionthe aquous layer was extracted with EtOAc (2×50 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationthe solids were filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-6e6c6649663d451a9666e2bcb9ec1c8d
出典データセット
uspto-grants-2007_09
特許番号
US07265122B2

関連ノート

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