Ethanol → HCID 59292850, compound

HRID 2409773Notes

Reaction equation

HRID 2409773 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 59292850HCID 59292850, compound

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-070f7d1b826b49f29e24dbfcf6d737f6
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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