Methanol → 1-(2-Methyl-pyridin-4-yl)-ethanone oxime

Temperatur

70 °C

To a stirred suspension of 4-acetyl-2-methyl-pyridine [CAS No. 2732-28-7] (9.7 g, 71.8 mmol) in water (115 ml) was added at room temperature hydroxylamine hydrochloride (8.48 g, 122 mmol) and the mixture was heated to 70° C. At this temperature methanol (145 ml) was added dropwise over a period of 15 min and afterwards a solution of sodium acetate trihydrate (25.4 g, 187 mmol) in water (115 ml) was added dropwise over a period of 15 min. The reaction mixture was stirred at 80° C. for 3.5 h, brine (150 ml) was added and the solution was extracted with ethyl acetate (2×250 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO4) and evaporated. The crude product was purified by crystallization from ethyl acetate/hexane to give 1-(2-methyl-pyridin-4-yl)-ethanone oxime (7.25 g, 67%) as an off-white solid; mp 154° C.

1. extractionthe solution was extracted with ethyl acetate (2×250 ml)
2. washThe combined organic layers were washed with brine (150 ml)
3. dry with materialdried (MgSO4)
4. customevaporated
5. customThe crude product was purified by crystallization from ethyl acetate/hexane

ORD-Eintrag

ord-b77cabe33af04792a1dd03c65ea168da

Quelldatensatz

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07514443B2