Ethanol → ethyl quinoline-2-carboxylate

HRID 1803770ノート

反応式

HRID 1803770 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH2:19][CH3:20])=[O:12]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7124Quinaldic Acid

生成物 1

HCID 421739ethyl quinoline-2-carboxylate

実験手順

Quinoline-2-carboxylic acid (Aldrich, 10.0 g, 57.7 mmol) was added to ethanol (500 mL) and sulfuric acid (25 mL) and refluxed for 7 hours. The mixture was concentrated under reduced pressure and dichloromethane (400 mL) was added. The organic layer was washed twice with saturated sodium bicarbonate (400 mL), dried with sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (t, J=7.12 Hz, 3H), 4.43 (q, J=7.12 Hz, 2H), 7.76 (ddd, J=8.14, 6.95, 1.19 Hz, 1H), 7.88 (ddd, J=8.48, 6.95, 1.53 Hz, 1H), 8.11 (m, 2H), 8.18 (d, J=8.48 Hz, 1H), 8.58 (d, J=8.48 Hz, 1H). MS (DCI) m/z 202.05 (M+H)1.

後処理

  1. temperaturerefluxed for 7 hours
  2. concentrationThe mixture was concentrated under reduced pressure and dichloromethane (400 mL)
  3. additionwas added
  4. washThe organic layer was washed twice with saturated sodium bicarbonate (400 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ccb15996bca34e0dad3395686ae02d81
出典データセット
uspto-grants-2013_01
特許番号
US08350083B2

反応ノート

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