Hydrogen Peroxide → 9H-Indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trione

HRID 129442

Reaction equation

HRID 129442 reaction equation
[N:1]1[C:2]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:3]=2[NH:4][C:5](=[O:7])[CH:6]=1.[OH:16]O>C(O)(=O)C.C(OC(=O)C)(=O)C>[NH:1]1[C:6](=[O:16])[C:5](=[O:7])[NH:4][C:3]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:2]1=2

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 190359769H-Indeno[1,2-b]pyrazine-3,9(4H)-dione

Product 1

HCID 190359779H-Indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trioneYield 79.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Procedure

9H-Indeno[1,2-b]pyrazine-3,9(4H)-dione (20 g, 100.9 mmol), recrystallized from acetic acid, was suspended in a mixture of 135 ml acetic acid and 135 ml acetic anhydride and hydrogen peroxide (9.8 ml, 35%) was added. After stirring overnight another portion (9.8 ml, 35%) of hydrogen peroxide was added. This was repeated five times over a week. The red precipitate was filtered off, washed with acetic acid and water and dried to give 18.5 g (79.6%) of the title compound, which could be further purified by dissolving in aqueous sodium hydroxide and precipitation by hydrochloric acid. M.p. >300° C. 1H-NMR (DMSO-d6, δ): 7.15-7.45 (m, 4H), 12 (s, 1H), 12.8 (s,1H).

Workup

  1. additionwas added
  2. additionwas added
  3. customover a week
  4. filtrationThe red precipitate was filtered off
  5. washwashed with acetic acid and water
  6. customdried

Sources & evidence

ORD record
ord-971dcb27339942aba522e1e9dfeadbe7
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Linked notes

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