Phosphorus oxychloride → 6-bromo-2-chloro-N-methyl-4-nitropyridin-3-amine
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][CH3:12])=[CH:4][N+:3]=1[O-].P(Cl)(Cl)([Cl:16])=O>>[Br:1][C:2]1[N:3]=[C:4]([Cl:16])[C:5]([NH:11][CH3:12])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
A suspension of 2-bromo-5-(methylamino)-4-nitropyridine 1-oxide (3.35 g, 13.51 mmol) in phosphorous oxychloride (35 mL, 374 mmol) was heated at 110° C. After 1 h, the reaction mixture was cooled to r.t. and evaporated to dryness in vacuo. The residue was partitioned between EtOAc (100 mL) and saturated sodium hydrogen carbonate, the layers were separated and the organic layer was washed with brine and dried over MgSO4. The residue was purified by flash column chromatography (SiO2, 0% EtOAc/Hexanes to 30% EtOAc/hexanes) to give 6-bromo-2-chloro-N-methyl-4-nitropyridin-3-amine 2.59.