Reaktion #70204

Reaktionsgleichung

ketone

3′-Hydroxy-4′-methoxyacetophenone

compound 19

O-(4-Nitrobenzyl)hydroxylamine Hydrochloride

pyridine

→

CP30218

Ausbeute 89.6%

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

Ausbeute 89.6%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture heated
2. 2
   Temperaturat reflux for 3 h
3. 3
   Temperaturthen cooled
4. 4
   Sonstigethe solvent evaporated under reduced pressure
5. 5
   SonstigeThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
6. 6
   ExtraktionThe separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml)
7. 7
   Trocknenthe combined organic fractions were dried (MgSO4)
8. 8
   Filtrationthen filtered
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    Sonstigeto give a light-yellow solid
11. 11
    SonstigeRecrystallisation (isopropanol) of this material

Vorschrift

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.

Quelle