Ethanol → Ethyl 2-(3-methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetate

HRID 2423317

Reaktionsgleichung

Reaktionsgleichung von HRID 2423317
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:28][C:29]([OH:31])=[O:30])[CH:11]=[CH:12][C:13]=1[O:14][C:15]1[C:16]([N+:25]([O-:27])=[O:26])=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2.[CH3:32][CH2:33]O>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:11]=[CH:12][C:13]=1[O:14][C:15]1[C:16]([N+:25]([O-:27])=[O:26])=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 598648342-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

Produkt 1

HCID 59864865Ethyl 2-(3-methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetate

Versuchsvorschrift

Concentrated sulfuric acid (0.32 mL, 11.3 mmol) was added to 24.2 (4 g, 11.3 mmol) in EtOH. The mixture was heated to reflux for 15 h. After cooling, EtOH was evaporated under vacuum, and the residue was treated with EtOAc (100 mL). Saturated NaHCO3 was added to neutralize the acid. The organic layer was separated, dried with MgSO4 and concentrated to give 24.3. MS ESI (pos.) m/z: 383.1 (M+H). 1H NMR (DMSO-d6) δ 8.99 (dd, 1H); 8.24 (m, 2H); 7.77 (dd, 1H); 7.29 (d, 1H); 7.21 (d, 1H); 7.18 (d, 1H); 6.96 (dd, 1H); 4.13 (q, 2H); 3.73 (s, 5H); 1.23 (t, 3H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 h
  3. temperatureAfter cooling
  4. customEtOH was evaporated under vacuum
  5. additionthe residue was treated with EtOAc (100 mL)
  6. additionSaturated NaHCO3 was added
  7. customThe organic layer was separated
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-93fc0c8368b94319aaeb41600691f435
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960567B2

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