2-Amino-6-methoxy-3-nitropyridine → HCID 178419698, Verbindung

HRID 916744

Reaktionsgleichung

Reaktionsgleichung von HRID 916744
[Br:1]C1N=C(N)C([N+]([O-])=O)=CC=1.C[O:13][C:14]1[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1>Br.C(O)(=O)C>[BrH:1].[NH2:20][C:18]1[N:19]=[C:14]([OH:13])[CH:15]=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22]

Komponenten

4

Edukt 2

HCID 38524282-Amino-6-methoxy-3-nitropyridineHCID 120977456-Bromo-3-nitro-2-pyridinamine

Produkt 1

HCID 178419698HCID 178419698, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Bromo-3-nitro-pyridin-2-ylamine. To a glass pressure vessel containing 6-methoxy-3-nitro-pyridin-2-ylamine (5.0 g, 29.5 mmol) was added 30% hydrogen bromide/acetic acid (60 mL). The vessel was sealed, and the contents were heated to 60° C. for 24 h. The reaction mixture was cooled, and the solvent was removed in vacuo giving 6.8 g (>95%) of crude 6-amino-5-nitro-pyridin-2-ol hydrobromide (HPLC: Rt=5.46). This material (2.0 g, 8.5 mmol) was taken up in toluene (30 mL), followed by phosphorus pentoxide (2.4 g, 17.0 mmol) and tetrabutyl ammonium bromide (3.2 g, 9.7 mmol). The mixture was heated to reflux for 4 h. The reaction mixture was cooled to 0° C., diluted with saturated NaHCO3, and extracted with ethyl acetate (3×100 mL). The combined organics were washed with water (100 mL) and dried (Na2SO4) to afford 1.18 g (64%) of 6-bromo-3-nitro-pyridin-2-ylamine.

Aufarbeitung

  1. customThe vessel was sealed
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef282a0871e9489fae960e26493665f9
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271261B2

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