Ethyl Acetate → 2,5-Dichloro-4-methoxyquinoline

HRID 430090노트

반응식

HRID 430090 반응식
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1.[O:14]([CH3:16])[K].CCOC(C)=O>CO>[Cl:1][C:2]1[CH:11]=[C:10]([O:14][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 183536682,4,5-TrichloroquinolineHCID 178502595HCID 178502595, 화합물

생성물 1

HCID 183537032,5-Dichloro-4-methoxyquinoline

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To 2.4,5-trichloroquinoline (0.79 g, 3.4 mmol) was added KOMe (20.4 ml of a 0.5 M suspension in MeOH). The mixture was heated under reflux for 2.5 h. EtOAc was added and the solution was allowed to cool to room temperature. The solvent was evaporated in vacuo and the residue submitted to column chromatography (silica gel, EtOAc:hexanes 1:6→1:3). 4,5-Dichloro-2-methoxyquinoline eluted first, then 2,4,5-trichloroquinoline. followed by the title compound, a colourless solid, (0.43 g, 44%). δH (CDCl3) 4.04 (s, 3H), 6.77 (s, 1H), 7.50-7.60 (m, 2H), 7.85 (dd, J=6.7, 3.0, 1H); MS (AP+) 228 (MH+, 100%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customThe solvent was evaporated in vacuo
  4. wash4,5-Dichloro-2-methoxyquinoline eluted first

출처 및 근거

ORD 기록
ord-92851fa35ffa4a28b7a52e576c33192d
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

반응 노트

불러오는 중…