Phosphorus oxychloride → Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

HRID 495466ノート

反応式

HRID 495466 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2O.O=P(Cl)(Cl)[Cl:21].P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2[Cl:21]

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178469588HCID 178469588、化合物

生成物 1

HCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a stirred solution of the crude 6-methoxy-4-hydroxy-3-ethoxycarbonylquinoline (Step A, 74 g, 0.25 M) in dry toluene (300 mL) was added POCl3 (46.6 mL, 0.5 mol) followed by PCl5 (26 g, 0.125 mol). The mixture was heated at reflux for 6 h. The toluene and the excess of POCl3 were removed under vacuum. The solid residue was suspended into a mixture of 1N NaOH and ice. The resulting solid was filtered off, washed several times with water, then with a minimum amount of MeOH, and dried over P2O5 to give 6-methoxy-4-chloro-3-ethoxycarbonylquinoline as a white solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. customThe toluene and the excess of POCl3 were removed under vacuum
  4. additionThe solid residue was suspended into a mixture of 1N NaOH and ice
  5. filtrationThe resulting solid was filtered off
  6. washwashed several times with water
  7. dry with materialwith a minimum amount of MeOH, and dried over P2O5

出典と根拠

ORDレコード
ord-1730f8fe5bb944a8ac2c86950b4070b0
出典データセット
uspto-grants-2005_09
特許番号
US06939874B2

反応ノート

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