Dimethylformamide → Methyl 2,3-dichloroisonicotinate

To a suspension of 2,3-dichloro-isonicotinic acid (7.7 g, 40 mmol) in dichloromethane (45 mL) were added DMF (0.1 mL) and oxalyl chloride (17.5 mL, 200 mmol). The reaction mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The resultant residue was azeotroped with toluene, then cooled to 0° C. and dissolved in methanol (135 mL). The mixture was allowed to warm to room temperature and then concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate and the resulting solution was washed with a saturated solution of sodium hydrogen carbonate, water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a colourless oil that crystallised on standing (7.9 g, 96%). 1H NMR (CDCl3, 400MHz) 8.38 (d, J=5.0 Hz, 1H), 7.52 (d, J=5.0 Hz, 1H), 3.99 (s, 3H).

1. concentrationconcentrated under reduced pressure
2. customThe resultant residue was azeotroped with toluene
3. temperaturecooled to 0° C.
4. dissolutiondissolved in methanol (135 mL)
5. temperatureto warm to room temperature
6. concentrationconcentrated under reduced pressure
7. customto give a residue
8. washthe resulting solution was washed with a saturated solution of sodium hydrogen carbonate, water and brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated

ORD-Eintrag

ord-41fa149862384b4dafebd116f34ccb3b

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08293763B2