4-Aminobenzonitrile → HCID 68422362, compound

Participants

Reaction Steps

After adding 17 ml of trimethylsilyl cyanide to a suspension of 17.4 g of 5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (Example 41c), 9.68 g of 4-aminobenzonitrile, 17 g of MS3A, 5 g of Yb(OTf)3 in 400 ml of THF, the mixture was stirred at room temperature for 14 hours. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was washed with an ethyl acetate and heptane mixed solvent to give 4-{[cyano-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl]amino}benzonitrile (28.01 g).

Provenance & Evidence