Dimethyl Sulfoxide → Ethyl 2-(3-nitropyridin-4-yl)acetate

Temperatur

100 °C

To a 100 ml RB flask was added 1.5 g (5.3 mmol) of 3-nitro4-pyridinyl-propanedioic acid diethyl ester, 0.450 g (10.6 mmol) of lithium chloride, 0.095 g (5.3 mmol) of water and 35 mL of DMSO. The solution was heated at 100° C. for 4 h. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed successively with water (50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated, and the residue was chromatographed on silica gel eluting with a hexane-10% EtOAc/hexane gradient to give 0.76 g of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 1.14 (t, J=7.1 Hz, 3H), 4.06 (q, J=7.1 Hz, 2H), 4.12 (s, 2H), 7.63 (d, J=4.9 Hz, 1H), 8.82 (d, J=4.9 Hz, 1H), 9.21 (s, 1H); C9H10N2O4: APES+MS m/z 211 (M+H).

1. customThe cooled reaction mixture
2. washwashed successively with water (50 mL) and brine (50 mL)
3. dry with materialThe organic phase was dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customthe residue was chromatographed on silica gel eluting with a hexane-10% EtOAc/hexane gradient

ORD-Eintrag

ord-1c22ce7af6b941d6af528c521012d145

Quelldatensatz

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06815439B2