(3-Fluoro-6-nitro-2-vinylphenyl)-(1-methylallyl)amine → 5-Fluoro-2-methyl-8-nitro-1,2-dihydroquinoline

Participants

Reaction Steps

To a solution of (3-fluoro-6-nitro-2-vinylphenyl)-(1-methylallyl)amine (134 mg, 0.567 mmol) in DCM (10 mL) was added Grubbs catalyst (2nd generation, benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium) (9.6 mg, 0.011 mmol). The reaction mixture was stirred at RT for 64 h, and then purified by column chromatography (Si—PCC, eluant 1-4% EtOAc in cyclohexane) affording recovered starting material (56 mg) and the title compound (62.8 mg). The recovered starting material was dissolved in DCM (10 mL) and Grubbs catalyst (2nd generation, benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium) (12 mg) was added. The reaction mixture was stirred at 45° C. for 16 h, and then purified by column chromatography (Si—PCC, DCM). The combined products were further purified by column chromatography (Si—PCC, eluant 1.5-4% EtOAc in cyclohexane) affording the title compound as a red solid (76.8 mg, 65%). 1H NMR (CDCl3, 300 MHz): 8.26 (1H, bs), 7.92 (1H, dd, J=9.6, 6.0 Hz), 6.53 (1H, dd, J=10.2, 1.7 Hz), 6.24 (1H, dd, J=9.7, 8.4 Hz), 5.70-5.65 (1H, m), 4.72-4.63 (1H, m), 1.43 (3H, J=6.6 Hz)

Provenance & Evidence