Hydrochloric Acid → 1-carboxymethyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione
Reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=[O:15])[C:9](=[O:14])[N:10]2[OH:13])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].P([O-])([O-])([O-])=O.Br[CH2:26][C:27]([OH:29])=[O:28].Cl>C(O)C>[C:27]([CH2:26][O:13][N:10]1[C:11]2[C:6](=[CH:5][C:4]([C:16]([F:19])([F:17])[F:18])=[C:3]([C:1]#[N:2])[CH:12]=2)[NH:7][C:8](=[O:15])[C:9]1=[O:14])([OH:29])=[O:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 0.3 g (1.1 mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione in 30 ml ethanol was added 30 ml 0.5M phosphate buffer pH 7.4. The mixture was added 0.9 g (6.5 mmol) bromoacetic acid and then stirred at 25° C. for 10 days. 4N hydrochloric acid was added to pH 1, and then the reaction mixture was evaporated in vacuo. The residue was stirred with water to give 0.27 g (74%) of 1-carboxymethyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione. M.p. 257° C. 1H-NMR (DMSO-d6): 8.2 (1H, s), 7.6 (1H, s), 4.8 (2H, s).
Workup
- customthe reaction mixture was evaporated in vacuo
- stirringThe residue was stirred with water
Sources & evidence
- ORD record
- ord-2fcd0c9acece4741b78aaafaeafb5537
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05061706
Reaction notes
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