Methanol → 4-[3-(Ethyloxy)-4-nitrophenyl]-1-propylpyridinium acetate

Participants

Reaction Conditions

Reaction Steps

To 1-(2,4-dinitrophenyl)-4-[3-(ethyloxy)-4-nitrophenyl]pyridinium chloride (1.2 g, 2.57 mmol) in 10 mL of MeOH was added, propylamine (0.151 g, 2.57 mmol). The mixture was heated to 100° C. for 4 h. The mixture was cooled and rotovaped down. The product was taken up in acetone. This solution was loaded onto a short silica gel column and eluted with EtOAc (˜500 mL) to remove the aniline by product. The product was then eluted with 300 mL of (10% HOAc/10% MeOH/80% DCM). The solvent was rotovaped down to give the title compound of step C (0.84 g, 2.42 mmol, 94%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (d, J=6.96 Hz, 2H), 8.63 (d, J=6.96 Hz, 2H), 8.07 (d, J=8.42 Hz, 1H), 7.90 (d, J=1.65 Hz, 1H), 7.74 (dd, J=8.42, 1.83 Hz, 1H), 4.59 (t, J=7.23 Hz, 2H), 4.38 (q, J=7.08 Hz, 2H), 1.91-2.00 (m, 2H), 1.86 (s, 3H), 1.35 (t, J=6.96 Hz, 3H), 0.89 (t, J=7.33 Hz, 3H).

Provenance & Evidence