Reaction #5001

Reaction equation

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate

hydroxyamine hydrochloride

potassium acetate

→

aimed compound

Yield 72.0%

methyl 2-[[4,6-dimethoxypyrimidin-2-yl)oxy]-6-(hydroxyiminomethyl)benzoate

Yield 72.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.DISTILLATIONMethanol was distilled off under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   WashThe organic layer was washed with water, 5% hydrochloric acid
4. 4
   Dryinga saturated salt aqueous solution, and was dried with magnesium sulfate anhydride
5. 5
   FiltrationAfter filtering
6. 6
   workup.ADDITIONa small amount of Florisil was added to the resultant product
7. 7
   workup.STIRRINGwas stirred for 5 minutes
8. 8
   FiltrationThe Florisil was filtered out
9. 9
   workup.DISTILLATIONethyl acetate was distilled off under reduced pressure

Procedure

2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate, 0.8 g of hydroxyamine hydrochloride, 1.1 g of potassium acetate and 10 ml of methanol were placed in a 50 ml eggplant type flask, and were stirred for 10 minutes at room temperature. Methanol was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, 5% hydrochloric acid and a saturated salt aqueous solution, and was dried with magnesium sulfate anhydride. After filtering, a small amount of Florisil was added to the resultant product, and was stirred for 5 minutes. The Florisil was filtered out, and ethyl acetate was distilled off under reduced pressure to obtain 1.5 g of the aimed compound (refractive index=1.5558) at a yield of 72%.

Source