Hydrogen Peroxide → HCID 67767514, compound

HRID 742090Notes

Reaction equation

HRID 742090 reaction equation
[OH:1][CH:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][CH:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].CO.OO>O>[OH:1][CH:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=[C:3]1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 14798Sodium HydroxideHCID 14665444HCID 14665444, compound

Product 1

HCID 67767514HCID 67767514, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.23 g (0.96 mmol) 3-hydroxy-2-phenyl-2H, 3H, 4H-1-benzopyridin-4-one, 0.94 g NaOH (in 4 mL water) and 35 mL MeOH was added 15 mL of H2O2 over ice bath. The yellow solution was then stirred at room temperature for 4 hours before the mixture was poured into 300 mL of water. The resulting mixture was extracted with CH2Cl2 and the solvent was removed from the organic phase. The resulting residue was recrystallized form toluene which gave the desired product in 17% yield. MP: 260°-262° C. Quantum yield (relative to 3-hydroxyflavone in CH2Cl2) 1.4. Extinction coefficient εmax (M-1 cm-1) 10,000. λmax (abs)=343 nm and λmax (em)=510 nm.

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2
  2. customthe solvent was removed from the organic phase
  3. customThe resulting residue was recrystallized form toluene which

Sources & evidence

ORD record
ord-f33a993426bd4db7a9b5cfa96db3ef37
Source dataset
uspto-grants-1996_09
Patent number
US05552551

Reaction notes

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