Butanedione → 7-Amino-8-chloro-2,3-dimethyl-quinoxaline-6-carboxylic acid methyl ester

HRID 2039612Notes

Reaction equation

HRID 2039612 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([Cl:12])[C:5]=1[NH2:13].[CH3:15][C:16](=O)[C:17](=O)[CH3:18].CCOC(C)=O>CCO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[C:6]([Cl:12])[C:5]=1[NH2:13])[N:11]=[C:17]([CH3:18])[C:16]([CH3:15])=[N:10]2)=[O:14]

Participants

5

Reactant 3

HCID 650ButanedioneHCID 8857Ethyl AcetateHCID 578559942,4,5-Triamino-3-chloro-benzoic acid methyl ester

Product 1

HCID 578559197-Amino-8-chloro-2,3-dimethyl-quinoxaline-6-carboxylic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.5 g (6.96 mmol) of 2,4,5-triamino-3-chloro-benzoic acid methyl ester in 27 ml of EtOH, is added 0.81 ml (9.18 mmol) of 2,3-butanedione. The mixture is stirred under reflux during 1 hour. After cooling the mixture to ambient temperature EtOAc is added and the organic phase is washed with H2O (2 times). The organic phase is dried on Na2SO4, filtrated and evaporated. After purification by flash chromatography on silica gel, 1.18 g (4.22 mmol, 62%) of an orange-coloured solid were obtained. 1H-NMR (CDCl3, 300 MHz): ? ppm=2.67 (s, 3H), 2.75 (s, 3H), 3.97 (s, 3H), 6.47 (s br, 2H), 8.58 (s, 1H).

Workup

  1. temperatureunder reflux during 1 hour
  2. additionis added
  3. washthe organic phase is washed with H2O (2 times)
  4. customThe organic phase is dried on Na2SO4
  5. filtrationfiltrated
  6. customevaporated
  7. customAfter purification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1976bc22b6d7426abf9e944027ec306b
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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