Diphenyl Ether → 8-bromo-3-methyl-5-nitroquinolin-4(1H)-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH:12]=[C:13]([CH3:18])[C:14]([O:16]C)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]2[C:3]=1[NH:11][CH:12]=[C:13]([CH3:18])[C:14]2=[O:16]Participants
3
Conditions
- Temperature
- 250 °C
Procedure
A mixture of methyl 3-[(2-bromo-5-nitrophenyl)amino]-2-methylprop-2-enoate (Compound 304F, 10 g, 3.2 mmol) and PhOPh (6 mL) was stirred at 250° C. for 2 h. The reaction mixture was allowed to cool to room temperature. Petroleum ether (60 mL) was added to the reaction mixture and the precipitate was filtered. The material was purified by column chromatography to afford 2.8 g of the desired product (yield: 28%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ=1.95 (s, 3 H), 7.48 (d, J=8.0 Hz, 1 H), 7.91 (s, 1 H), 8.12 (d, J=8.0 Hz, 1 H), 11.46 (s, br, 1 H).