Benzoyl Peroxide → HCID 178526471, compound

HRID 1696528Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([OH:14])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-nitro-3,4-dihydroquinolin-2(1H)-one (0.46 g, 2.4 mmol) and NBS (0.53 g, 3.0 mmol) in CHCl3 (20 mL) was added benzoyl peroxide (cat. amount) at RT. The mixture was refluxed at 80° C. for 3 h. More NBS (0.25 g) was added and the reaction mixture was refluxed at 80° C. for 1 h. The solvent was evaporated and the residue was dissolved in EtOH. The solid was filtered, washed with EtOH and dried under vacuum to obtain 6-nitroquinolin-2-ol as a pale yellow solid (0.36 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.71 (d, J=−2.0 Hz, 1H), 8.34 (dd, J=2.8, and 9.2 Hz, 1H), 8.14 (d, J=9.6 Hz, 1H), 7.44 (d, J=9.2 Hz, 1H), 6.68 (dd, J=1.6, and 9.6 Hz, 1H). LC-MS (EI) m/z: 191.0 (M+H+).

Workup

temperaturethe reaction mixture was refluxed at 80° C. for 1 h
customThe solvent was evaporated
dissolutionthe residue was dissolved in EtOH
filtrationThe solid was filtered
washwashed with EtOH
customdried under vacuum

Sources & evidence

ORD record: ord-6a2ddfabfaba4e4b809f9d57e74bd478
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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