N-bromobutanimide → 5-Bromo-3-nitro-1-phenylpyridin-2(1H)-one

HRID 547679Notes

Reaction equation

HRID 547679 reaction equation
[N+:1]([C:4]1[C:5](=[O:16])[N:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:17]N1C(=O)CCC1=O>CN(C)C=O>[Br:17][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5](=[O:16])[N:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 223191573-Nitro-1-phenyl-1,2-dihydropyridin-2-one

Product 1

HCID 223191565-Bromo-3-nitro-1-phenylpyridin-2(1H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 ml of a dimethylformamide solution containing 1 g of 3-nitro-1-phenyl-1,2-dihydropyridin-2-one was incorporated with 988 mg of N-bromosuccinimide, followed by stirring at room temperature overnight. Further, it was stirred at 50° C. for 3 hours. The reaction mixture was poured into ice-water, and the resulting precipitates were collected by filtration, to give 1.27 g of the title compound.

Workup

  1. stirringFurther, it was stirred at 50° C. for 3 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-a871a130fca74ce68fac5b7fdeef119d
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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