Hydrochloric Acid → HCID 19990472, compound

HRID 346158Notes

Reaction equation

HRID 346158 reaction equation
[C:1]([NH:8][C:9]1[C:14]([N+:15]([O-])=[O:16])=[CH:13][C:12]([Cl:18])=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=1)([C:3](OCC)=[O:4])=[O:2].Cl>CN(C)C=O.[Pt]>[Cl:18][C:12]1[CH:13]=[C:14]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:4])[N:15]2[OH:16])=[CH:10][C:11]=1[C:19]([F:22])([F:21])[F:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19990425HCID 19990425, compound

Product 1

HCID 19990472HCID 19990472, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.0 g (5.9 mmol) N-ethoxalyl-4-chloro-6-nitro-3-trifluoromethylaniline in 50 ml dimethylformamide was hydrogenated at atm. pressure by using 200 mg 5% Pt-C as a catalyst. The reaction mixture was stirred with 4N hydrochloric acid and the crude product was filtered off. The crude product was dissolved in 25 ml 1N potassium hydroxide and the solution was acidified with concentrated hydrochloric acid. The precipitate was filtered off to give 310 mg 19%) of 7-chloro-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione. M.p. decomp. MS (m/e): 280, 1H-NMR (DMSO-d6): 12.2 (1H, broad s), 7.6 (2H, m).

Workup

  1. filtrationthe crude product was filtered off
  2. dissolutionThe crude product was dissolved in 25 ml 1N potassium hydroxide
  3. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-5b54fbd4a7d5451296b3220228e35b47
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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