Butanedione → HCID 22037030, compound

HRID 2217297Notes

Reaction equation

HRID 2217297 reaction equation
[CH3:1][C:2](=O)[C:3](=O)[CH3:4].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[NH2:16][C:17]1[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])([O-])=O.[K+].[K+]>O>[CH3:1][C:2]1[C:3]([CH3:4])=[N:16][C:17]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=[CH:26][C:27]=2[N:28]=1

Participants

6

Reactant 4

HCID 650ButanedioneHCID 11430Potassium CarbonateHCID 656671Sodium PyrosulfiteHCID 11171330Ethyl 2,3-diaminobenzoate

Product 1

HCID 22037030HCID 22037030, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

2,3-Butanedione (0.0776 mol) was added at room temperature to a solution of sodium pyrosulfite (0.1 mol) in water (75 ml). The mixture was heated to 70° C. and then added to a solution of ethyl 2,3-diaminobenzoate (0.0776 mol) in water (75 ml). The mixture was stirred at 100° C. for 12 hours, cooled, basified with K2CO3 10% and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (17.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 93/7; 20-45 μm). The pure fractions were collected and the solvent was evaporated, yielding 12 g (67%) of ethyl 2,3-dimethyl-5-quinoxalinecarboxylate (interm. 6).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (17.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 93/7; 20-45 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-24fc2c28bf56419fa62ff204a5d6cd25
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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