Dichloromethane → HCID 22504090, compound

Participants

Reaction Steps

2-Benzyloxy-6-methoxy-3 nitro-pyridine (3.41 g, 13.1 mmol) was shaken with 1 g Rainey nickel in 100 mL THF in a Parr hydrogenation apparatus at 48 psi H2 for 20 h. TLC analysis (silica, CH2Cl2) indicated complete consumption of starting material. The reaction mixture was filtered and concentrated. The crude product was purified by gradient elution flash chromatography (SiO2, 1:1 CH2Cl2/hexanes to 3:1 CH2Cl2/hexanes to 100% CH2Cl2) to give 1.65 g (7.17 mmol, 55%) of 2-benzyloxy-6-methoxy-pyridin-3-ylamine. MS (APCI) m/z 231.2 (M+1). 1H NMR (300 MHz) CDCl3 7.29-7.48 (m, 5H), 6.98 (d, J=8.1 Hz, 1H), 6.19 (d, J=8.1 Hz, 1H), 5.42 (s, 2H), 3.84 (s, 3H).

Provenance & Evidence