Tetrahydrofuran → HCID 53844231, compound

HRID 343806Notes

Reaction equation

HRID 343806 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8](Cl)[C:9](Cl)=[N:10]2.[O:19]1[CH2:23]CCC1>C(OCC)(=O)C>[NH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([O:19][CH3:23])[C:9]([O:2][CH3:1])=[N:10]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 53808462HCID 53808462, compound

Product 1

HCID 53844231HCID 53844231, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (25% solution in methanol, 13.9 ml, 61 mmol) was added over 12 minutes to a stirred solution of 5-amino-2,3-dichloro-6,7-dimethylquinoxaline (6.15 g, 25.4 mmol) in dry tetrahydrofuran (250 ml) under nitrogen at 0° C. The mixture was stirred at 0° C. for 20 minutes, and at room temperature for 72 hours. The mixture was diluted with ethyl acetate (750 ml), washed with water (2×250 ml) and brine (250 ml), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/dichloromethane) to give 5-amino-2,3-dimethoxy-6,7-dimethylquinoxaline (4.55 g, 77%) as a white solid, mp 166°-167° C.

Workup

  1. waitat room temperature for 72 hours
  2. washwashed with water (2×250 ml) and brine (250 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution with hexane/dichloromethane)

Sources & evidence

ORD record
ord-a95b0a32f7f24ff78cf5cb16b5cbdeaf
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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