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Michael Addition

(Aza-Michael Addition)


Example 1

A solution of benzylamine (11.2 g, 104 mmol) and crotonitrile (7.0 g, 110 mmol) in EtOH (125 mL) was heated to reflux for 24 h. The mixture was cooled to RT, concentrated, and purified by silica gel chromatography to provide the product. [13 g, 73%]

[Patent Reference: WO2016014463, page 67, (6.7 MB)]

Example 2

A mixture of 3-Bromoaniline (10.00 g, 58.14 mmol) and methyl acrylate (5.30 mL, 58.14 mmol) in AcOH (0.4 mL) was refluxed for 16 h. The mixture was concentrated and the resulting residue was purified by silica gel column chromatography (1:10 to 1:6 PE/EtOAc) to provide the product as a red liquid. [11.92 g, 80%]

[Patent Reference: WO2015089337, page 205, (17.5 MB)]