Reaction #70211

Reaction equation

4′-Hydroxy-3′-methoxyacetophenone

compound 19

O-(4-Nitrobenzyl)hydroxylamine Hydrochloride

→

CP30261

Yield 55.3%

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

Yield 55.3%

Conditions

Workup

1. 1
   TemperatureAfter being heated for 3 h the reaction mixture
2. 2
   Temperaturewas cooled
3. 3
   Otherthe solvent removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe ensuing residue was dissolved in CH2Cl2 (20 mL)
5. 5
   Washwashed with H2O (2×15 mL)
6. 6
   Dryingthen dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe residue thus obtained
10. 10
    Washwas subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution)

Procedure

4′-Hydroxy-3′-methoxyacetophenone (25) (150 mg, 0.903 mmol) was condensed with compound 19 (0.203 g, 0.992 mmol) according to the general procedure II-A defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (20 mL), washed with H2O (2×15 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The residue thus obtained was subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution) to afford the title compound CP30261 (158 mg, 55%) as a yellow solid, m.p. 118.4-121.1° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Source