HCID 19990424, compound → HCID 19990440, compound

HRID 346149Notes

Reaction equation

HRID 346149 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=O)([C:3](OCC)=[O:4])=[O:2]>CN(C)C=O.[Pt]>[OH:19][N:17]1[C:10]2[C:9](=[CH:14][C:13]([O:15][CH3:16])=[CH:12][CH:11]=2)[NH:8][C:1](=[O:2])[C:3]1=[O:4]

Participants

4

Reactant 1

HCID 19990424HCID 19990424, compound

Product 1

HCID 19990440HCID 19990440, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

0.21 g (0.8 mmol) N-ethoxalyl-5-methoxy-2-nitroaniline in 10 ml dimethylformamide was hydrogenated at atm. pressure by using 10 mg 5% Pt-C as a catalyst. The reaction mixture was filtered and 5 drops of 25% aqueous ammonia was added to the filtrate. The precipitate was filtered off, and the filter cake was washed several times with 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 0.07 g (44%) of 1-hydroxy-6-methoxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d ) 12.1 (1H, broad s), 7.6-6.6 (3H, m), 3.8 (3H, s). MS (m/e): 208 (M+, 50%), 163 (100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition5 drops of 25% aqueous ammonia was added to the filtrate
  3. filtrationThe precipitate was filtered off
  4. washthe filter cake was washed several times with 1N aqueous potassium hydroxide
  5. filtrationthe precipitate was filtered off
  6. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-7916a51546de4d45a477fd00d5c34e41
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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