Methanol → 2-Chloro-4-methoxy-6-methylquinoline

HRID 430086노트

반응식

HRID 430086 반응식
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[OH-:14].[K+].[CH3:16]O>>[Cl:1][C:2]1[CH:11]=[C:10]([O:14][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 27546682,4-Dichloro-6-methylquinoline

생성물 1

HCID 183537192-Chloro-4-methoxy-6-methylquinoline

실험 절차

To 2,4-dichloro-6-methylquinoline (4.1 g, 19 mmol) in methanol (34 ml) was added KOH (1.42 g) and the resulting solution was heated under reflux for 2.5 h. The mixture was concentrated in vacuo and partitioned between ethyl acetate and half-concentrated brine. The organic layer was concentrated and chromatographed (silica gel, EtOAc:hexanes 1:5→1:3). 4-Chloro-2-methoxy-6-methylquinoline eluted first, then 2,4-dichloro-6-methylquinoline, followed by the colourless crystalline title compound, (1.97 g, 49%). δH (CDCl3) 2.52 (s, 3H), 4.05 (s, 3H), 6.71 (s, 1H), 7.53 (dd, J=8.6, 2.0, 1H), 7.83 (d, J=8.6, 1 H), 7.90 (br, s, 1 H); MS (AP+) 208 (MH+, 100%).

후처리

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 2.5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate and half-concentrated brine
  5. concentrationThe organic layer was concentrated
  6. customchromatographed (silica gel, EtOAc:hexanes 1:5→1:3)
  7. wash4-Chloro-2-methoxy-6-methylquinoline eluted first

출처 및 근거

ORD 기록
ord-e9625519c4b2439a980f784e91b06e6a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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