Butanedione → HCID 22037030, compound

HRID 1789997Notes

Reaction equation

HRID 1789997 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-a0f99a5dfa9a45848a8856bf58a18c6e
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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