Acetic Acid → 5-(2-Methoxy-6-methyl-pyridin-3-yl)-2H-pyrazol-3-ylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile (21 g, 110.4 mmol) in ethanol (200 mL) is placed in a sealed tube, Hydrazine, hydrate (32.1 mL, 662.4 mmol) and acetic acid (21.0 mL) are added and the reaction heated at 100° C. for 2 h. The solvent is evaporated off and the reaction mixture is diluted with EtOAc (500 mL) and saturated sodium bicarbonate solution (100 mL). The organic layer is separated and the aqueous layer is extracted with EtOAc (2×250 mL). The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude product which is taken into the next step without any further purification. Yield=16.5 g (73%). 1H NMR (400 MHz, DMSO-d6) δ 11.50 (bs, 1H), 7.90 (d, J=7.6 Hz, 1H), 6.86 (d, J=7.6 Hz, 1H), 5.88 (s, 1H), 4.64 (s, 3H), 2.38 (s, 3H).

Provenance & Evidence