N-bromobutanimide → 6-BROMO-2,3-DIHYDROQUINOLIN-4(1H)-ONE

HRID 1296136Notes

Reaction equation

HRID 1296136 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[Br:12]N1C(=O)CCC1=O>ClCCl>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][C:4]2=[O:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1171582,3-dihydroquinolin-4(1H)-one

Product 1

HCID 7594476-BROMO-2,3-DIHYDROQUINOLIN-4(1H)-ONEYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−.

Workup

  1. customwas partitioned between aqueous sodium bicarbonate and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

Sources & evidence

ORD record
ord-68a4bd1a5cac476c8895a8165f78e9d0
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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