HCID 14391496, compound → HCID 19990441, compound

HRID 346139Notes

Reaction equation

HRID 346139 reaction equation
[C:1]([NH:8][C:9]1[CH:10]=[C:11]([C:20]#[N:21])[C:12](=[CH:15][C:16]=1[N+:17]([O-])=[O:18])[C:13]#[N:14])([C:3](OCC)=[O:4])=[O:2].[H][H]>CN(C)C=O.[Pd]>[C:20]([C:11]1[CH:10]=[C:9]2[C:16](=[CH:15][C:12]=1[C:13]#[N:14])[N:17]([OH:18])[C:3](=[O:4])[C:1](=[O:2])[NH:8]2)#[N:21]

Participants

5

Reactant 2

HCID 14391496HCID 14391496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19990441HCID 19990441, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.8 g (3.03 mmol) 4-ethoxalylamino-5-nitrophthalonitrile in 50 ml dimethylformamide was hydrogenated at atm. pressure by using 25 mg 5% Pd-C as a catalyst. When the hydrogen uptake had ceased, the reaction mixture was filtered and evaporated in vacuo. The residue was recrystallized (dimethylformamide-water) to give 0.4 g (66%) of 6,7-dicyano-1-hydroxy-quinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 7.97 (1H, s), 7.57 (1H, s). MS (m/e): 228 (M+, 80%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was recrystallized (dimethylformamide-water)

Sources & evidence

ORD record
ord-ef60c919f2bc4be7999d3fb7527064b3
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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