2-[(4-Nitro-2-vinylphenoxy)methyl]pyridine → 3-Ethyl-4-(pyridin-2-ylmethoxy)aniline

Participants

Reaction Steps

A mixture of 2-[(4-nitro-2-vinylphenoxy)methyl]pyridine (1.06 g, 4.16 mmol) and PtO2 (123 mg) in ethanol (100 ml) was stirred under an atmosphere of hydrogen until completion of the reaction (the reaction being complete when 4 mole equivalents of hydrogen have been reacted). After filtration on celite, the solvent was evaporated and the residue purified on silica gel (2% methanol/CH2Cl2) to give 3-ethyl-4-(pyridin-2-ylmethoxy)aniline (787 mg, 83%); NMR Spectrum: 1.12 (t, 3H), 2.53 (q, 2H), 4.56 (br s, 2H), 5.01 (s, 2H), 6.33 (dd, 1H), 6.43 (d, 1H), 6.69 (d, 1H), 7.32 (dd, 1H), 7.5 (d, 1H), 7.84 (t, 1H), 8.55 (d, 1H); Mass Spectrum: 229 (MH+).

Provenance & Evidence