Reacción #70204

Ecuación de reacción

ketone

3′-Hydroxy-4′-methoxyacetophenone

compound 19

O-(4-Nitrobenzyl)hydroxylamine Hydrochloride

pyridine

→

CP30218

Rendimiento 89.6%

(E)-3′-Hydroxy-4′-methoxyacetophenone O-4-Nitrobenzyl Oxime

Rendimiento 89.6%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture heated
2. 2
   Temperaturaat reflux for 3 h
3. 3
   Temperaturathen cooled
4. 4
   Otrothe solvent evaporated under reduced pressure
5. 5
   OtroThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
6. 6
   ExtracciónThe separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml)
7. 7
   Secadothe combined organic fractions were dried (MgSO4)
8. 8
   Filtraciónthen filtered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    Otroto give a light-yellow solid
11. 11
    OtroRecrystallisation (isopropanol) of this material

Procedimiento

A solution of ketone 12 (200 mg, 1.20 mmol) in EtOH (2.0 mL) was treated with compound 19 (0.27 g, 1.32 mmol) and pyridine (0.5 mL) and the resulting mixture heated at reflux for 3 h then cooled and the solvent evaporated under reduced pressure. The ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL). The separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml) and the combined organic fractions were dried (MgSO4) then filtered and concentrated under reduced pressure to give a light-yellow solid. Recrystallisation (isopropanol) of this material afforded the title compound CP30218 (340 mg, 89%) as pale-yellow crystals, m.p. 105.0-105.7° C.

Fuente