(2-Amino-4,5-dimethoxyphenyl)-(5-methylfuran-2-yl)methanone

A mixture of ketone 1 (1.00 g, 5 mmol) [1], iron powder (1.39 g, 24 mmol), glacial acetic acid (1.02 mL, 18 mmol), water (5 mL) and ethyl acetate (5 mL) was refluxed with stirring for 4-5 h (TLC monitoring). After that, the reaction mixture was neutralized with NaHCO₃, and the solid was filtered off. The solid was thoroughly washed with hot ethyl acetate. The filtrate was dried with Na₂SO₄, the solvent was evaporated under reduced pressure and the residue was recrystallized from the mixture of ethyl acetate:petroleum ether (1:0.6) to yield title compound 2 as pale yellow crystals (1.1 g, 85 %).

Mp: 160-161 °C.

IR (KBr): 3350, 1685, 1635 cm^-1.

¹H NMR (CDCl₃, 60 MHz, ppm): 2.42 (s, 3H, CH₃), 3.82 (s, 3H, OCH₃), 3.90 (s, 3H, OCH₃), 5.96 (s, 2H, NH₂), 6.18 (d, 1H, J = 3.2, 3-H_Fur), 6.20 (s, 1H, H_Ar), 7.04 (d, J = 3.2, 4-H_Fur), 7.56 (s, 1H, H_Ar).

Anal. calc. for C₁₄H₁₅NO₄: C 64.36, H 5.79, N 5.36; Found: C 64.39, H 5.66, N 5.47.