HCID 2880788, compound → HCID 19990403, compound

HRID 346147Notes

Reaction equation

HRID 346147 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[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][CH:13]=[C:12]([O:15][CH3:16])[CH:11]=2)[NH:8][C:1](=[O:2])[C:3]1=[O:4]

Participants

4

Reactant 1

HCID 2880788HCID 2880788, compound

Product 1

HCID 19990403HCID 19990403, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.10 g (0.4 mmol) N-ethoxalyl-4-methoxy-2-nitroaniline in 10 ml dimethylformamide was hydrogenated at atm. pressure by using 5% Pt-C (0.01 g) as a catalyst. The reaction mixture was filtered and 10 ml 1N hydrochloric acid was added. The reaction mixture was cooled to 0° C. and the precipitate was filtered off, washed with water, ethanol and ether to give 0.03 g (39%) of 1-hydroxy-7-methoxyquinoxaline-2,3(1H,4H)-dione. M.p. decomp. 1H-NMR (DMSO-d6): 12.0 (broad s), 7.0 (3H, m), 3.8 (3H, s). MS (m/e): 208 (M+, 70%), 163 (100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition10 ml 1N hydrochloric acid was added
  3. filtrationthe precipitate was filtered off
  4. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-9918878e76a54a208ac564c2199b45c6
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

Loading…