Reacción #65767

Ecuación de reacción

DMF

3,4-diethoxycarbonyl-2-hydroxy-6-(4-hydroxyphenyl)-5-nitropyridine

phosphorus oxychloride

DMF

→

2-Chloro-3,4-diethoxycarbonyl-6-(4-hydroxyphenyl)-5-nitropyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturathe mixture was heated for further 30 minutes
3. 3
   workup.DISTILLATIONAfter the solvent was distilled off
4. 4
   workup.ADDITIONice-water was added
5. 5
   Extracciónfollowed by neutralization with sodium hydrogencarbonate and extraction with ethyl acetate
6. 6
   LavadoAfter the organic layer was washed with water
7. 7
   Secadoa saturated aqueous solution of sodium chloride and dried
8. 8
   workup.DISTILLATIONthe solvent was distilled off
9. 9
   OtroThe residue was purified by silica gel column chromatography (eluent:ethyl acetate)

Procedimiento

In 2.5 ml of phosphorus oxychloride was suspended 130 mg of 3,4-diethoxycarbonyl-2-hydroxy-6-(4-hydroxyphenyl)-5-nitropyridine, whereto 0.4 ml of DMF was added. The mixture was heated at 100° C. for 30 minutes. Then, 0.4 ml of DMF was added and the mixture was heated for further 30 minutes. After the solvent was distilled off, ice-water was added, followed by neutralization with sodium hydrogencarbonate and extraction with ethyl acetate. After the organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried, the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent:ethyl acetate).

Fuente