Potassium Hydroxide → 3-Amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

At 0° C., a solution of tin chloride dihydrate (30.2 g) in concentrate aqueous HCl (150 mL) was added dropwise over 2 hours to a solution of 4-ethylamino-3-nitro-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (5.0 g) in DMF (100 mL). The mixture was further stirred for 1 hour at 5° C., then poured to a mixture of ice (900 g) and potassium hydroxide (440 g), extracted with ethyl acetate (2×1.4 L). The combined organic layers were washed with brine (700 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (4,56 g) as a solid. 1H NMR (DMSO-d6) δ: 8.30-8.20 (m, 2H); 7.75-7.60 (m, 2H); 7.08 (s, 1H); 6.11 (t, J=6 Hz, 1H); 5.95 (br. s, 2H); 3.4-3.3 (m, 2H); 1.27 (t, J=7 Hz, 3H).

Provenance & Evidence