Reaction #70204

Reaction equation

ketone

3′-Hydroxy-4′-methoxyacetophenone

compound 19

O-(4-Nitrobenzyl)hydroxylamine Hydrochloride

pyridine

→

CP30218

Yield 89.6%

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

Yield 89.6%

Solvents

EtOH

Conditions

Workup

1. 1
   Temperaturethe resulting mixture heated
2. 2
   Temperatureat reflux for 3 h
3. 3
   Temperaturethen cooled
4. 4
   Otherthe solvent evaporated under reduced pressure
5. 5
   OtherThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
6. 6
   ExtractionThe separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml)
7. 7
   Dryingthe combined organic fractions were dried (MgSO4)
8. 8
   Filtrationthen filtered
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    Otherto give a light-yellow solid
11. 11
    OtherRecrystallisation (isopropanol) of this material

Procedure

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.

Source