HCID 22614896, compound → 5-Amino-6,7-dichloro-2,3-dimethoxyquinoxaline

HRID 842702Notes

Reaction equation

HRID 842702 reaction equation
[Cl:1][C:2]1[C:3]([N+:17]([O-])=O)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2>O1CCCC1.C(OCC)(=O)C.ClCCl.[Pd]>[NH2:17][C:3]1[C:2]([Cl:1])=[C:11]([Cl:12])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:15][CH3:16])[C:7]([O:13][CH3:14])=[N:8]2

Participants

6

Reactant 1

HCID 22614896HCID 22614896, compound

Product 1

HCID 106066205-Amino-6,7-dichloro-2,3-dimethoxyquinoxalineYield 78.5%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dichloro-2,3-dimethoxy-5-nitroquinoxaline (20 g, 0.066 mol) and 5% w/w palladium-on-carbon (50% wet) (1.2 g) were suspended in a mixture of tetrahydrofuran (0.12 L) and ethyl acetate (0.12 L). The mixture was hydrogenated at 60° C. and 414 kPa (60 psi) for 22 hours, cooled, diluted with dichloromethane (0.48 L) and the catalyst removed by filtration through celite (trade mark) filter aid. The solution was concentrated under reduced pressure with the gradual addition of toluene. The mixture was then filtered and the solid was washed with toluene (20 ml) to give the title compound as a brown solid (14.2 g, 78%), m.p. 182-4° C.

Workup

  1. customwas hydrogenated at 60° C.
  2. temperaturecooled
  3. customthe catalyst removed by filtration through celite (trade mark)
  4. filtrationfilter aid
  5. concentrationThe solution was concentrated under reduced pressure with the gradual addition of toluene
  6. filtrationThe mixture was then filtered
  7. washthe solid was washed with toluene (20 ml)

Sources & evidence

ORD record
ord-61df4a5765e142f98012c1f9ac80c9ee
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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