HCID 19808452, compound → HCID 19990411, compound

HRID 1494355Notes

Reaction equation

HRID 1494355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=[O:9])=[C:4]([NH:11][C:12]([C:14]([O:16]CC)=O)=[O:13])[CH:3]=1>CN(C)C=O.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([OH:9])[C:14](=[O:16])[C:12](=[O:13])[NH:11]2

Participants

4

Reactant 1

HCID 19808452HCID 19808452, compound

Product 1

HCID 19990411HCID 19990411, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g (7.3 mmol) 4-chloro-2-ethoxalylamino-1-nitrobenzene in 50 ml dimethylformamide was hydrogenated at atm. pressure by using Ra-Ni (0.2 g) as a catalyst. The reaction mixture was filtered and evaporated in vacuo. The residue was stirred with water to give a crude product. Recrystallization (dimethylformamide-water) gave 1.2 g (78%) 6-chloro-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. >300° C. M.p. >300° C. 1H-NMR (DMSO-d6): 11.8 (2H, broad s), 7.2 (3H, m). MS (m/e): 212 (M+, 60%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customto give a crude product
  4. customRecrystallization (dimethylformamide-water)

Sources & evidence

ORD record
ord-21e04260e1774fd9bd2723b5740b4704
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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