Ammonia → HCID 22419806, compound

HRID 346136Notes

Reaction equation

HRID 346136 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([N+:10]([O-])=[O:11])[C:5]([NH:13][C:14]([C:16]([O:18]CC)=O)=[O:15])=[CH:4][CH:3]=1.CN(C)C=O.N>O1CCCC1.[Pd]>[ClH:1].[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]2[C:5]([NH:13][C:14](=[O:15])[C:16](=[O:18])[N:10]2[OH:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 19990450HCID 19990450, compound

Product 2

HCID 313Hydrochloric AcidHCID 22419806HCID 22419806, compoundYield 142.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g (3.36 mmol) 6-chloro-3-ethoxalylamino-2-nitrobenzonitrile in 75 ml tetrahydrofuran was added 25 ml dimethylformamide and 1.0 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 100 mg 5% Pd-C as a catalyst. The precipitated product 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 0.57 g (72%) of 7-chloro-8-cyano-1-hydroxyquinoxaline-2,3(1H,4H)-dione. M.p. 280° C. decomp H-NMR (DMSO-d6) 12.3 (2H, broad s), 7.5 (2H, s). MS (m/e): 237 (M+, 10%).

Workup

  1. filtrationThe precipitated product 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-a94e0cce5571497bbd6c67472c605282
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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