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

HRID 914964

반응식

HRID 914964 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6e6c6649663d451a9666e2bcb9ec1c8d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265122B2

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