HCID 19990451, compound → HCID 19990438, compound

HRID 346160Notes

Reaction equation

HRID 346160 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[C:11]([Cl:17])[C:10]=1[N+:18]([O-:20])=O)([C:3](OCC)=[O:4])=[O:2]>C(O)C.[Pt]>[OH:20][N:18]1[C:10]2[C:9](=[CH:14][C:13]([Cl:15])=[C:12]([Cl:16])[C:11]=2[Cl:17])[NH:8][C:1](=[O:2])[C:3]1=[O:4]

Participants

4

Reactant 1

HCID 19990451HCID 19990451, compound

Product 1

HCID 19990438HCID 19990438, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.0 g (5.9 mmol) N-ethoxalyl-2-nitro-3,4,5-trichloroaniline in 50 ml ethanol was hydrogenated at atm. pressure by using 70 mg Pt-C (5%) as a catalyst. The precipitate was filtered off and the filter cake was washed with 10 ml 1N aqueous potassium hydroxide. The filtrate was acidified with concentrated hydrochloric acid and the precipitate was filtered off, washed with water, ethanol and ether to give 0.18 g (11%) of 1-hydroxy-6,7,8-trichloroquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 7.4 (1H, s) MS m/z: 280 (M+, trace, 3Cl), 265 (35%), 237 (100%), 173 (55%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe filter cake was washed with 10 ml 1N aqueous potassium hydroxide
  3. filtrationthe precipitate was filtered off
  4. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-890950bdddac44368e804f7391cb28c4
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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