Pyridine → 5,6-Dihydroxy-4,7-dinitro-2-benzofuran-1(3H)-one

HRID 1881216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881216
[OH:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[O:11]C)[C:7](=[O:16])[O:6][CH2:5]2.[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1>C(OCC)(=O)C>[OH:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[OH:11])[C:7](=[O:16])[O:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 86633446HCID 86633446, Verbindung

Produkt 1

HCID 159832325,6-Dihydroxy-4,7-dinitro-2-benzofuran-1(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Hydroxy-6-methoxy-4,7-dinitro-3H-isobenzofuran-1-one (210 mg) was dissolved in ethyl acetate (2.5 ml) followed by addition of aluminum chloride (132 mg) in nitrogen atmosphere. Pyridine (265 μl, 3.28 mmol) was added dropwise. The resulting mixture was heated to reflux for 2 hours, and then quenched with water (0.5 ml) and conc. HCl (0.5 ml) at 75° C. Ethyl acetate (15 ml) was added and phases were separated. The aqueous layer was extracted once with ethyl acetate (15 ml). The combined organic layers were dried over anhydrous Na2SO4. The product was filtrated, evaporated to dryness and recrystallized from heptane-toluene-ethyl acetate.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customquenched with water (0.5 ml) and conc. HCl (0.5 ml) at 75° C
  4. additionEthyl acetate (15 ml) was added
  5. customphases were separated
  6. extractionThe aqueous layer was extracted once with ethyl acetate (15 ml)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. filtrationThe product was filtrated
  9. customevaporated to dryness
  10. customrecrystallized from heptane-toluene-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ef1a3079441b41da83ce2fad7cbe8a8c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318785B2

Notizen zur Reaktion

Wird geladen…