Hydrogen Peroxide → HCID 19035966, compound

HRID 263908Notes

Reaction equation

HRID 263908 reaction equation
[OH:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[N:13]=[CH:12][C:11](=[O:15])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[C:22](OC(=O)C)(=[O:24])[CH3:23].OO>C(O)(=O)C>[C:22]([O:1][C:2]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]2[N:13]=[CH:12][C:11](=[O:15])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 19035967HCID 19035967, compound

Product 1

HCID 19035966HCID 19035966, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-Hydroxy-9-phenyl-9H-indeno[1,2-b]pyrazin-3(4H)-one (0.24 g) was stirred with a mixture of acetic acid (3 ml), acetic anhydride (3 ml) and hydrogen peroxide (0.42 ml) at room temperature for 3 weeks. The resulting very complex mixture was evaporated and treated with water resulting in precipitation of 200 mg of a crystalline mixture. Purification on silica gel column using methylene chloride/methanol: (9/1) as eluent resulted in 70 mg of a compound which was recrystallized from ethanol. Yield 40 mg of the title compound. M.p. 220°-223° C. MS showed the molecular ion 318 and a degradation pattern in accordance with the title compound. 1H-NMR (CDCl3 /CD3OD: 9/1, δ): 2.4-2.5 (3H, s), 7.3-7.6 (9H, m), 7.9-8.0 (1H, m), 8.2 (1H, s).

Workup

  1. customThe resulting very complex mixture was evaporated
  2. additiontreated with water resulting in precipitation of 200 mg of a crystalline mixture
  3. customPurification on silica gel column

Sources & evidence

ORD record
ord-2940ab7e93c04ef0bebefe3014a46b86
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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