Water → ethyl 2,3-dimethylquinoxaline-6-carboxylate

HRID 1498902Notes

Reaction equation

HRID 1498902 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH2:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].O>C(O)C>[CH3:3][C:2]1[C:12]([CH3:11])=[N:1][C:2]2[C:12](=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)[N:13]=1

Participants

4

Reactant 2

HCID 962WaterHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 2826621ethyl 2,3-dimethylquinoxaline-6-carboxylateYield 203.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3,4-diaminobenzoate (500 mg, 2.77 mmol) and diacetyl (238 mg, 2.77 mmol) were dissolved in ethanol (20 ml), and the mixture was heated under reflux. One hour after, diacetyl (30 mg) was added thereto, and the mixture was heated under reflux. After the mixture was heated under reflux for 2.5 hours in total, the reaction solution was poured into water, and the precipitate was separated by filtration and washed with water. By through circulation drying for 15 hours, the title compound (650 mg, quantitative) as a light-brown powder was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. additionOne hour after, diacetyl (30 mg) was added
  4. temperaturethe mixture was heated
  5. temperatureunder reflux
  6. temperatureAfter the mixture was heated
  7. temperatureunder reflux for 2.5 hours in total, the reaction solution
  8. customthe precipitate was separated by filtration
  9. washwashed with water
  10. customBy through circulation drying for 15 hours

Sources & evidence

ORD record
ord-f07b1b93eab54beaad10684964d97d1c
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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