Ammonia → 6,7-dichloro-N-hydroxy-1,4-dihydroquinoxaline-2,3-dione

HRID 346130Notes

Reaction equation

HRID 346130 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=[O:10])=[C:4]([NH:12][C:13]([C:15]([O:17]CC)=O)=[O:14])[CH:3]=1.CN(C)C=O.N>O1CCCC1.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[N:9]([OH:10])[C:15](=[O:17])[C:13](=[O:14])[NH:12]2

Participants

7

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 19958578ethyl-N-(4,5-dichloro-2-nitro-phenyl)oxamate

Product 2

HCID 313Hydrochloric AcidHCID 101059926,7-dichloro-N-hydroxy-1,4-dihydroquinoxaline-2,3-dioneYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.4 g (1.3 mmol) 4,5-dichloro-2-ethoxalylamino-1-nitrobenzene in 30 ml tetrahydrofuran was added 10 ml dimethylformamide and 0.4 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 50 mg 5% Pd-C as a catalyst. The precipitate was filtered off and washed with tetrahydrofuran. The filter cake was washed several times with 5% aqueous potassium hydroxide. Acidification of the filtrate with 4N hydrochloric acid gave 0.14 g (45%) of 6,7-dichloro-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 12.2 (2H, m), 7.50 (1H, s), 7.27 (1H, s). MS (m/e): 246 (M+, 35%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with tetrahydrofuran
  3. washThe filter cake was washed several times with 5% aqueous potassium hydroxide

Sources & evidence

ORD record
ord-887623e747a14ccf91e4aad0eb2ecfc6
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

Loading…