Ammonia → HCID 19990465, compound

HRID 346172Notes

Reaction equation

HRID 346172 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=[O:11])[C:7]([NH:13][C:14]([C:16]([O:18]CC)=O)=[O:15])=[CH:6][C:3]=1[C:4]#[N:5].CN(C)C=O.N>O1CCCC1.[Pd]>[Cl:1][C:2]1[CH:9]=[C:8]2[C:7]([NH:13][C:14](=[O:15])[C:16](=[O:18])[N:10]2[OH:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 19990462HCID 19990462, compound

Product 1

HCID 19990465HCID 19990465, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.6 g (2.0 mmol) 2-chloro-5-ethoxalylamino-4-nitrobenzonitril in 50 ml tetrahydrofuran was added 15 ml dimethylformamide and 0.7 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 0.1 g Pd-C as a catalyst. The catalyst was filtered off, and the filter cake was washed with tetrahydrofuran. The precipitated product was dissolved in 1N aqueous potassium hydroxide. Addition of concentrated hydrochloric acid to pH 1 gave 0.25 g (50%) 7-chloro-6-cyano-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. 320° C. decomp. 1H-NMR (DMSO-d6): 7.6 (1H, s), 7.5 (1H, s).

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe filter cake was washed with tetrahydrofuran
  3. dissolutionThe precipitated product was dissolved in 1N aqueous potassium hydroxide
  4. additionAddition of concentrated hydrochloric acid to pH 1

Sources & evidence

ORD record
ord-39e0ab03bf3345249d688d2cae87226f
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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