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

HRID 2391922노트

반응식

HRID 2391922 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-682a7ce62eb84af9b02df49f8bbbb4e7
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273882B2

반응 노트

불러오는 중…