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

HRID 430086ノート

反応式

HRID 430086 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e9625519c4b2439a980f784e91b06e6a
出典データセット
uspto-grants-2001_11
特許番号
US06320051B1

反応ノート

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