HCID 86689782, compound → HCID 86689783, compound

Participants

Reaction Steps

To a solution of 3-methoxy-6-nitro-2-(prop-1-en-2-yl)pyridine (824 mg, 4.24 mmol) in ethanol (14.1 mL) was added 10% palladium on carbon (45.2 mg, 424 μmol). The reaction mixture was evacuated and back filled with hydrogen. This was repeated two more times. The reaction was stirred under hydrogen at 1 atm for 16 h. The mixture was then filtered reaction through a pad of celite, the filtrate concentrated in vacuo, and then purified by chromatography (silica, 10 to 60% ethyl acetate in hexanes) to give 6-isopropyl-5-methoxypyridin-2-amine (562 mg, 3.38 mmol, 80%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.04 (d, J=8.7 Hz, 1H), 6.33 (d, J=8.7 Hz, 1H), 4.12 (br. s, 2H), 3.78 (s, 3H), 3.36 (m, 1H), 1.22 (d, J=7.0 Hz, 6H); MS (EI/CI) m/z: 166.8 [M+H].

Provenance & Evidence