N-bromobutanimide → HCID 58938526, compound

HRID 598093Notes

Reaction equation

HRID 598093 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:26])[CH:12]=[CH:13][N:14]2[CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22].[Br:27]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:27][C:12]1[C:11](=[O:26])[C:10]2[C:15](=[CH:16][CH:17]=[CH:18][C:9]=2[C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[N:14]([CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58938552HCID 58938552, compound

Product 1

HCID 58938526HCID 58938526, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-(2,4-Dimethylphenyl)-1-(1-propylbutyl)quinolin-4(1H)-one, (0.21 g, 0.61 mmol), was dissolved in N,N-dimethylformamide (10 mL). The solution was cooled to 0° C. and N-bromosuccinimide (0.11 g, 0.62 mmol) was added. After 10 minutes, the solution was diluted with water, extracted with ethyl acetate, dried (Na2SO4), and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave 0.136 g (53% yield) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-60b150d0cc9147a0ac075da6f4afd937
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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