Diphenyl Ether → 8-bromo-3-methyl-5-nitroquinolin-4(1H)-one

HRID 511542Notes

Reaction equation

HRID 511542 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

Reactant 2

HCID 7583Diphenyl EtherHCID 67254564Methyl 3-[(2-bromo-5-nitrophenyl)amino]-2-methylprop-2-enoate2×

Product 1

HCID 672543158-bromo-3-methyl-5-nitroquinolin-4(1H)-oneYield 309.1%

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).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitate was filtered
  3. customThe material was purified by column chromatography

Sources & evidence

ORD record
ord-4530bf14fa5c4a9c8ceceda330fa4672
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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