Sodium Carbonate → 1-(3,4-Dimethoxyphenyl)ethan-1-amine

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Reaction Steps

3′,4′-Dimethoxyacetophenone oxime (1 gram, 5.1 mmol) was dissolved in 10 milliliters of glacial acetic acid, the solution was flushed with N2 and the palladium on carbon (0.2 grams, 5%) was added. The mixture was treated with 60 psi of H2 in a Parr Type Shaker for 24 hours. The catalyst was filtered off and the filtrate was concentrated to afford a yellow oil which was taken up in water, basified to pH 12 with a saturated solution of sodium carbonate and extracted with methylene chloride. The combined extracts were dried over magnesium sulfate and concentrated to afford 1.97 grams (82%) of product as a yellow oil: 1H NMR (CDCl3) δ7.02-6.75 (m, 3H), 4.08 (q, J1=6.6 Hz, J2=13.1 Hz, 1 H), 3.89 (s, 3H), 3.87 (s, 3H), 1.37 (d , J=6.6 Hz, 3H).

Provenance & Evidence