6,7-Dinitro-2,3-dihydro-1,4-benzodioxine → 7-Nitro-2,3-dihydro-1,4-benzodioxin-6-amine

HRID 2077729

Reaktionsgleichung

Reaktionsgleichung von HRID 2077729
[N+:1]([C:4]1[C:13]([N+:14]([O-])=O)=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]>[Fe].C(O)(=O)C>[N+:1]([C:4]1[C:13]([NH2:14])=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 1

HCID 35898126,7-Dinitro-2,3-dihydro-1,4-benzodioxine

Produkt 1

HCID 6072087-Nitro-2,3-dihydro-1,4-benzodioxin-6-amineAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 6,7-dinitro-2,3-dihydrobenzo[1,4]dioxin (Takakis, I. M.; Hadjimihalakis, P. M. J. Heterocyclic. Chem., 1991, 28, 625., 13 g, 57.8 mmol) and acetic acid (150 mL) was added iron powder (9.6 g, 172.5 mmol) at room temperature, then the mixture was refluxed for 30 min. After cooling, the mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2) to afford 3.22 g (28%) of the title compound as orange solid: 1H-NMR (CDCl3) δ 7.67 (1H, s), 6.23 (1H, s), 5.85 (2H, br.s), 4.19-4.33 (4H, m).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 30 min
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-e4dd782e349749ab9e3c088b5f30c980
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928119B2

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