Benzoyl Peroxide → HCID 14171574, compound

HRID 1639259Notes

Reaction equation

HRID 1639259 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[N:8]([CH:13]=[CH:14][CH:15]=3)[N:9]([CH3:12])[C:10]=2[CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:35]N1C(=O)CCC1=O.[Al]>C1COCC1>[Br:35][C:13]1[N:8]2[N:9]([CH3:12])[C:10]3[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[C:6](=[O:16])[C:7]2=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5359268AluminumHCID 14171569HCID 14171569, compound

Product 1

HCID 14171574HCID 14171574, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one (6.0 g) and a catalytic amount of dibenzoyl peroxide in 100 ml of THF was added portionwise N-bromosuccinimide (4.63 g) over 15 min. The flask was covered with aluminum foil and the solution was stirred at room temperature for 24 hrs. The solution was then concentrated and the residue was purified by HPLC (silica, dichloromethane) to give 7.10 g of a light green powder. This powder was recrystallized from ethanol to give 5.7 g of a yellow fibrous material, mp 133°-135°.

Workup

  1. concentrationThe solution was then concentrated
  2. customthe residue was purified by HPLC (silica, dichloromethane)

Sources & evidence

ORD record
ord-8536324ae7ee413bbb30b78cdb66fe55
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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