Benzoyl Peroxide → HCID 22724073, compound

HRID 2231062Notes

Reaction equation

HRID 2231062 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[C:16](=[O:17])[C:15]([CH3:18])=[N:14][C:13]3[CH:19]=[CH:20][CH:21]=[N:22][C:12]2=3)[CH:8]=[CH:9][CH:10]=1)=[O:4].[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:23][CH2:18][C:15]1[C:16](=[O:17])[N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[C:12]2[N:22]=[CH:21][CH:20]=[CH:19][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22724132HCID 22724132, compound

Product 1

HCID 22724073HCID 22724073, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-(3-methoxycarbonylphenyl)-2-methyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (5.02 g), N-bromosuccinimide (4.0 g) and benzoyl peroxide (0.50 g) in chloroform (60 ml) was stirred under reflux for 2 hours. The mixture was concentrated and chromatographed on silica gel column (1% methanol in chloroform) to give 2-bromomethyl-4-(3-methoxycarbonylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (4.75 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe mixture was concentrated
  3. customchromatographed on silica gel column (1% methanol in chloroform)

Sources & evidence

ORD record
ord-8f56e2c7322b4276a7c3c5da55333f25
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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