m-Chloroperbenzoic acid → HCID 66620274, compound

HRID 415559Notes

Reaction equation

HRID 415559 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]3[N:25]4[CH2:26][CH2:27][CH2:28][N:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:24]4=[N:23][C:18]=3[CH:19]=[N:20]2)=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.O>[Br:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]3[N:25]4[CH2:26][CH2:27][CH2:28][N:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:24]4=[N:23][C:18]=3[CH:19]=[N+:20]2[O-:9])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 66620899HCID 66620899, compound

Product 1

HCID 66620274HCID 66620274, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

MCPBA (800 mg of approximately 60% pure material) was added to a solution of tert-butyl 3-bromo-10,11-dihydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline-8(9H)-carboxylate (940 mg, 2.3 mmol) in chloroform (50 mL). The reaction was stirred for one hour at room temperature, and an analysis by LC/MS indicated the presence of starting material. Additional MCPBA (540 mg) was added, and the reaction was stirred for an additional 30 minutes and then diluted with water and chloroform. The aqueous layer was separated and extracted twice with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 0.97 g of tert-butyl 3-bromo-5-oxido-10,11-dihydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline-8(9H)-carboxylate.

Workup

  1. stirringthe reaction was stirred for an additional 30 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted twice with chloroform
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a0e7f465530415987e26fdf86336a60
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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