Potassium Permanganate → 2-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid

HRID 1494348Notes

Reaction equation

HRID 1494348 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:12][C:13]([OH:15])=[O:14])[CH2:3]1.[Mn]([O-])(=O)(=O)=[O:17].[K+]>O.[OH-].[Na+]>[C:13]([CH2:12][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:11][C:2](=[O:1])[C:3]1=[O:17])([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 3101125(3-Oxo-3,4-dihydroquinoxalin-1(2H)-yl)acetic acid

Product 1

HCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acidYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3.0 g (15 mmol) 1,2,3,4-tetrahydro-3-oxoquinoxaline-1-acetic acid in 50 ml water was added gradually a solution of 4. 0 g (25 mmol) potassium permanganate in aqueous sodium hydroxide (4%, w/v) and the mixture was refluxed for 4 h. The reaction mixture was cooled, filtered and the filtrate acidified with concentrated hydrochloric acid to pH 2.5. The precipitate was filtered off and washed with water to give 2.2 g (69%) 1-carboxymethylquinoxaline-2,3(1H,4H)- dione. M.p. >300° C. 1H-NMR (DMSO-d6): 12.0 (1H, broad s), 7.2 (4H, s), 7.0-5.0 (1H, broad s), 4.9 (2H, s).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. filtrationThe precipitate was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-e0781f4b79494452bb472794fe8585fa
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

Loading…