N,N-Diethylaniline → 2-chloro-3-ethoxypyridine

Temperatur

150 °C

A mixture of 3-ethoxy-pyridin-2-ol (4.0 g, 28.8 mmol, 1.0 equiv), N,N-diethylaniline (4.61 mL, 4.29 g, 28.8 mmol, 1.0 equiv) and phosphorus oxychloride (2.62 mL, 4.41 g, 28.8 mmol, 1.0 equiv) was heated to 150° C. under microwave irradiation for 20 min. The crude reaction mixture was poured into water (100 mL), the solution adjusted to pH 7 and extracted with dichloromethane (3×100 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1) providing 3.2 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 3H), 4.12 (q, J=7.0 Hz, 2H), 7.18 (d, J=3.2 Hz, 2H), 7.98 (t, J=3.2 Hz, 1H). MS (ISP): 157.7 [M+H]+.

1. customThe crude reaction mixture
2. extractionextracted with dichloromethane (3×100 mL)
3. dry with materialThe combined organic phases were dried over MgSO4
4. customthe solvent removed by evaporation under reduced pressure
5. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1)

ORD-Eintrag

ord-2946bd3eaef945f7b7678199de872183

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07645753B2