Sodium Hydroxide → 5-Bromo-1-oxo-1lambda~5~-quinoline

HRID 2175210Notes

Reaction equation

HRID 2175210 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1C=C(Cl)C=C(C(OO)=[O:20])C=1.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N+:7]2[O-:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 8173215-Bromoquinoline

Product 1

HCID 593983225-Bromo-1-oxo-1lambda~5~-quinolineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromoquinoline (2.5 g, 12.02 mmol) in DCM (50 mL) was added m-CPBA (3.50 g, 15.62 mmol) in three portions at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 3 h. After this time, 1N NaOH (40 ml) was added to the reaction, and the resulting mixture was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (2.7 g, 99% yield) as light yellow solid. LCMS, [M+H]+=223.9. 1H NMR (400 MHz, CDCl3) δ 8.75 (d, J=8.8 Hz, 1H), 8.65 (d, J=6.0 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 7.95 (d, J=7.7 Hz, 1H), 7.68-7.56 (m, 1H), 7.44 (dd, J=8.2, 6.0 Hz, 1H).

Workup

  1. additionUpon completion of addition
  2. extractionthe resulting mixture was extracted with DCM (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4dc1c58adb4043f6a72c77d98a280a75
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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