Ammonia → AC-7739 free base

Participants

Reaction Steps

A solution was prepared by dissolving (Z)-3,4,4′,5-tetramethoxy-3′-nitrostilbene (raw material 5) (8.63 g, 25.0 mmol) in acetonitrile (100 ml) succeeded by addition of ammonium formate (5.21 g, 82.6 mmol, 330 mole % to the above nitrostilbene derivative (raw material 5)), 5% platinum on carbon (water-content: 60.91%, 4.99 g, 0.50 mmol as platinum) and aqueous ammonia (28%, 1.69 ml, 25 mmol) to be reacted at 30° C. for 23 hours in an argon atmosphere. At the conclusion of the reaction, the catalyst and the insoluble matter were separated by filtration and the filtrate was subjected to quantitative analysis by HPLC. Formation of the objective substance, (Z)-2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)vinyl]aniline (objective substance 6; represented by the above formula (6)) (6.52 g, 20.7 mmol, 83%), was confirmed, as was formation of a by-product (E)-2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)vinyl]aniline (by-product 7; represented by the above formula (7)) (0.55 g, 1.73 mmol, 6.9%) and a by-product 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]aniline (by-product 8; represented by the above formula (8)) (0.52 g, 1.63 mmol, 6.5%). Formation was not observed for the by-product 2-(4-methoxy-3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethane (by-product 9; represented by the above formula (9)).

Provenance & Evidence