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

HRID 430090ノート

反応式

HRID 430090 の反応式
[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

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 183536682,4,5-TrichloroquinolineHCID 178502595HCID 178502595、化合物

生成物 1

HCID 183537032,5-Dichloro-4-methoxyquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-92851fa35ffa4a28b7a52e576c33192d
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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