Benzenamine, 3-ethynyl- → N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine

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Reaction Steps

4-chloro-7-fluoro-6-nitroquinazoline (12 g, 0.052 mol) was dissolved in 120 ml DCM. A solution of 3-ethynylaniline (7 g, 0.057 mol) in 200 ml isopropanol was added dropwise in an ice bath. The solution was stirred for 1 hour in the ice bath, then TEA (7 g, 0.069 mol) was added and allowed to stir for another 0.5 hour at room temperature. Yellow precipitate was formed and the solid was filtered and washed with 20 ml isopropanol twice, dried to give N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine 8.2 g as a yellow solid (50.3% yield).

Provenance & Evidence