Ethanol → 5-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

HRID 2409773ノート

反応式

HRID 2409773 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.OS(O)(=O)=O.[CH3:29][CH2:30]O>>[CH2:29]([O:22][C:21]([C:18]1[CH:19]=[CH:20][C:11]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=2)=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:23])[CH3:30]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 592928765-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid

生成物 1

HCID 592928505-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

実験手順

A mixture of 5-(3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.2) (2 g), H2SO4 conc. (0.6 mL) and EtOH (100 mL) was stirred at reflux for 30 h, allowed to cool and concentrated. The residue was diluted in EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 1.77 g of the title compound as a white solid. Title compound: ESI-MS: 338.2 [M+H]+; tR 3.81 min (System 1); TLC: Rf=0.29 (Hex/EtOAc, 3:2).

後処理

  1. temperatureat reflux for 30 h
  2. temperatureto cool
  3. concentrationconcentrated
  4. additionThe residue was diluted in EtOAc
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with H2O and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

出典と根拠

ORDレコード
ord-070f7d1b826b49f29e24dbfcf6d737f6
出典データセット
uspto-grants-2014_08
特許番号
US08815901B2

反応ノート

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