Methanol → Methyl quinoline-4-carboxylate

HRID 2187355

反応式

HRID 2187355 の反応式
S(Cl)(Cl)=O.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1.[CH3:18]O>>[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1

参加物

4

反応物 3

HCID 887MethanolHCID 102434-Quinolinecarboxylic acidHCID 24386Thionyl Chloride

生成物 1

HCID 3002895Methyl quinoline-4-carboxylate収率 42%

反応条件

温度
-2.5 °C

実験手順

Thionyl chloride (4.5 ml) was added dropwise, under argon to a cooled, stirring slurry of 4-quinolinecarboxylic acid (5.32 g) in methanol (120 ml) maintaining an internal temperature of 0 to −5° C. Once addition was complete the reaction mixture was heated at reflux for 16 h. After cooling to ambient temperature the volatiles were removed at reduced pressure and the residue partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The organic phase was washed with brine, dried (Na2SO4) and the solvent removed at reduced pressure to give the title compound as a pale yellow oil (4.82 g).

後処理

  1. additionOnce addition
  2. temperaturewas heated
  3. temperatureat reflux for 16 h
  4. temperatureAfter cooling to ambient temperature the volatiles
  5. customwere removed at reduced pressure
  6. customthe residue partitioned between saturated aqueous sodium bicarbonate and diethyl ether
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed at reduced pressure

出典と根拠

ORDレコード
ord-55adacad8aad49a78e6ae095e2e58d6f
出典データセット
uspto-grants-2002_06
特許番号
US06410529B1

関連ノート

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