Nitric Acid → 2,6-Dichloro-4-methyl-3-nitropyridine

Temperatur

0 °C

To a suspension of 2,6-dichloro-4-methylpyridine (1 g, 6.17 mmol) in trifluoroacetic acid anhydride (5 mL, 35.4 mmol) cooled down to 0° C. was added dropwise nitric acid (0.579 mL, 12.96 mmol) into it. The resulting solution was stirred at RT for 18 hr. The reaction mixture was added slowly to a chilled solution of sodium metabisulfite (1.183 g, 6.17 mmol) in water (8 mL) and stirred at RT for 2 hr. The reaction mixture was neutralized to pH 7 using 8N NaOH solution and extracted twice with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title product (1.187 g, 5.73 mmol, 93% yield) as white solid. tR: 1.07 min (LC-MS 2); ESI-MS: 208 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39 (s, 3H) 7.90 (s, 1H).

1. stirringstirred at RT for 2 hr
2. extractionextracted twice with CH2Cl2
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-71d0ad95dea74fa8bc97cdfae9d579f9

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08975417B2