Potassium Nitrate → 5'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide

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Reaction Steps

3'-Chloro-N-ethyl-4'-fluoroacetanilide (101 g, 0.468 mmol) is dissolved in conc. sulfuric acid (300 ml). A solution of potassium nitrate (57 g, 0.564 mol) in conc. sulfuric acid (220 ml) is added dropwise thereto at 5°. The solution obtained is stirred overnight, then poured on to ice/water and extracted with ethyl acetate (2×200 ml). The organic phase is washed in succession with water (200 ml), saturated sodium bicarbonate solution (100 ml) and saturated sodium chloride solution (100 ml). The organic phase is treated with active charcoal, filtered and dried over magnesium sulfate. The solvent is distilled off and the residue is recrystallized from ether/n-hexane. There are obtained 74.8 g (61%) of 5'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide with a m.p. of 68°.

Provenance & Evidence