Stannous chloride dihydrate → HCID 53486922, Verbindung

HRID 1713935

Reaktionsgleichung

Reaktionsgleichung von HRID 1713935
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:14]([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:14][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][C:2]=1[NH2:1]

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 70314200Methyl (2E)-3-(4-amino-3-nitrophenyl)prop-2-enoate

Produkt 1

HCID 53486922HCID 53486922, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl (2E)-3-(4-amino-3-nitrophenyl)acrylate (from Step 2, 1 eq) in ethanol (0.2 M) was added tin(II) chloride dihydrate (5.75 eq). The reaction mixture was heated to reflux for 8 h. At this time the reaction was allowed to cool to RT, concentrated and diluted with EtOAc. A saturated aqueous solution of NaHCO3 was added slowly. The mixture was stirred for 20 min; the organic layer was washed with brine, dried over Na2SO4 filtered and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 70% EtOAc in PE) to afford the title compound (57%). 1H-NMR (400 MHz; DMSO-<d6, 300 K) δ 3.67 (s, 3H), 4.59 (s, 2H), 5.17 (s, 2H), 6.08 (d, J 15.6, 1H), 6.5 (d, J 8.0, 1H), 6.74 (d, J 7.6, 1H), 6.82 (s, 1H), 7.39 (d, J 15.6, 1H); MS (ES+) m/z 193 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated
  4. additiondiluted with EtOAc
  5. additionA saturated aqueous solution of NaHCO3 was added slowly
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (SiO2; 70% EtOAc in PE)

Quellen und Nachweise

ORD-Eintrag
ord-470e5c6e7ae248d1aceea7284905a5fe
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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