N-[(4-methoxyphenyl)methyl]formamide

Synthesis

The general procedure for the synthesis of N-(4-methoxybenzyl)formamide by 1,4-dioxane-mediated microwave-assisted transamidation reaction using the compound (CAS:77287-34-4) and 4-methoxybenzylamine as raw materials was as follows: to a 10 mL microwave reaction vial, which was pre-oven-dried and fitted with a Teflon-coated magnetic stirring bar, were added sequentially formamide (1 mmol), 4- methoxybenzylamine (1 mmol) and undried 1,4-dioxane (2 mL). The reaction vial was sealed with a plastic microwave septum and stirred for 5 min at room temperature, then placed in the microwave reaction chamber and the reaction was carried out at the specified temperature and time. Upon completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, diluted by adding distilled water (10 mL) and subsequently extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and the filtrate was concentrated by rotary evaporator. The crude product was purified by column chromatography, and the eluent was a mixed solvent of ethyl acetate/hexane (10-20% volume fraction of ethyl acetate, adjusted according to the polarity of the product).

References

[1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 95, p. 11626 - 11628,3
[2] Chemical Communications, 2012, vol. 48, # 95, p. 11626 - 11628
[3] Tetrahedron Letters, 2013, vol. 54, # 20, p. 2553 - 2555
[4] RSC Advances, 2016, vol. 6, # 58, p. 52724 - 52728
[5] Journal of Molecular Catalysis A: Chemical, 2015, vol. 403, p. 15 - 26