Methanol → 4-Ethoxy-2-methylaniline

Participants

Reaction Steps

Compound 404a (250 mg, 1.38 mmol) was dissolved in EtOAc (10 mL) and MeOH (10 mL) and transferred to a 250 mL hydrogenation flask. 10% Pd/C (25 mg, 10% w/w) was added and the sample was hydrogenated for 4 h at 35 psi H2. Upon completion, the mixture was filtered over a bed of Celite and then concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with NaHCO3 (50 mL×3). The organic layer was dried over Na2SO4 to yield a dark-red oil (192 mg, 92%): TLC Rf 0.30 (20% EtOAc/hexanes). 1NMR (600 MHz, CDCl3) δ 6.67 (s, 1H), 6.62 (m, 2H), 3.97-3.93 (q, 2H, J=6.96 Hz), 3.42 (s, 2H), 2.16 (s, 3H), 1.38-1.35 (t, 3H, J=7.02 Hz). NMR (150 MHz, CDCl3) δ 152.3, 138.1, 124.4, 117.45, 116.34, 113.1, 64.2, 17.9, 15.2. Elemental analysis calculated for C9H13NO: C, 71.49; H, 8.67; N, 9.26. Found: C, 71.42; H, 8.76; N, 9.04.

Provenance & Evidence