Aniline → HCID 9816404, compound

HRID 1153731Notes

Reaction equation

HRID 1153731 reaction equation
[N:1]1[C:10]2[C:9](=[O:11])[CH:8]=[CH:7][C:6](=[O:12])[C:5]=2[N:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[NH:13]([C:8]1[C:9](=[O:11])[C:10]2[N:1]=[CH:2][CH:3]=[N:4][C:5]=2[C:6](=[O:12])[CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 113556455,8-Quinoxalinedione

Product 1

HCID 9816404HCID 9816404, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Approximately 2 g. of 5,8-quinoxalinedione were dissolved in 200 ml. of 2B ethanol. Aniline (1.2 g.) was added and the reaction was stirred overnight at room temperature. The reaction was evaporated, water was added, and the mixture was extracted several times with methylene chloride. The combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over a silica gel column, eluting with ethyl acetate. The desired fractions were combined and evaporated. The material was crystallized from ethyl acetate to give 50 mg. of the title product as a red powder, m.p. about 203°-205° C.

Workup

  1. customThe reaction was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted several times with methylene chloride
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed over a silica gel column
  7. washeluting with ethyl acetate
  8. customevaporated
  9. customThe material was crystallized from ethyl acetate
  10. customto give 50 mg

Sources & evidence

ORD record
ord-fbcec31f3cfc4447831a40bac5b73036
Source dataset
uspto-grants-1984_12
Patent number
US04486432

Reaction notes

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