Benzoyl Peroxide → 6-Bromoquinolin-2(1H)-one

HRID 1696538Notes

Reaction equation

HRID 1696538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide3×HCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 123789436-Bromoquinolin-2(1H)-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of commercially available 6-bromo-1,2,3,4-tetrahydro-2-quinolinone (5.0 g, 22 mmol) and NBS (4.9 g, 27 mmol) in CHCl3 (80 mL) was added a catalytic portion of benzoyl peroxide at RT. The mixture was refluxed at 80° C. for 3 h, after which additional NBS (2.0 g) was added and the reaction refluxed overnight at 80° C. Additional NBS (0.9 g) was added into the reaction mixture which was refluxed at 80° C. for 5 h. The solid was filtered, washed with EtOH and dried to yield 6-bromoquinolin-2(1H)-one (4.35 g, 88% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.93 (d, J=2.8 Hz, 1H), 7.88 (d, J=9.6 Hz, 1H), 7.64 (dd, J=2.0, and 8.8 Hz, 1H), 7.25 (d, J=8.8 Hz, 1H), 6.55 (dd, J=2.0, and 9.6 Hz, 1H); LC-MS (EI) m/z: 224.0 (M+H+).

Workup

  1. temperaturethe reaction refluxed overnight at 80° C
  2. temperaturewas refluxed at 80° C. for 5 h
  3. filtrationThe solid was filtered
  4. washwashed with EtOH
  5. customdried

Sources & evidence

ORD record
ord-eff5fa41c3ef4554a959d5b39267b2ea
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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