HCID 67833120, compound → HCID 19990437, compound

HRID 346173Notes

Reaction equation

HRID 346173 reaction equation
[C:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=O)[C:12]#[N:13])([C:3](OCC)=[O:4])=[O:2]>C(O)C.[Pt]>[C:12]([C:11]1[CH:10]=[C:9]2[C:16](=[CH:15][CH:14]=1)[N:17]([OH:19])[C:3](=[O:4])[C:1](=[O:2])[NH:8]2)#[N:13]

Participants

4

Reactant 1

HCID 67833120HCID 67833120, compound

Product 1

HCID 19990437HCID 19990437, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.5 g (1.9 mmol) 3-ethoxalylamino-4-nitrobenzonitril in 50 ml ethanol was hydrogenated at atm. pressure by using 25 mg 5% Pt-C as a catalyst. The catalyst was filtered off, and the filtrate was evaporated in vacuo. Cyclization was achieved by evaporation with acetic acid. Recrystallization (dimethylformamide-water) gave 0.25 g (65%) of 6-cyano-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. 250° C. decomp. 1H-NMR (DMSO-d6) 7.53 (s) and 7.40 (s)--a total of 3H.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customCyclization was achieved by evaporation with acetic acid
  4. customRecrystallization (dimethylformamide-water)

Sources & evidence

ORD record
ord-014f4982c4d74e97b996677603dae250
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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