HCID 66747421, compound → HCID 66747578, compound

HRID 1019986Notes

Reaction equation

HRID 1019986 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-])=O)=[C:5]([NH:11][CH2:12][C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>[Pd].CO>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([NH:11][CH2:12][C:13](=[O:14])[NH:16]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66747421HCID 66747421, compound

Product 1

HCID 66747578HCID 66747578, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (0.22 g, 2.06 mmol, 0.48 eq) is added at room temperature to a stirred solution of (3,4-dimethoxy-2-nitro-phenylamino)-acetic acid (1.1 g, 4.29 mmol, 1.0 eq) in methanol (30 mL). The mixture is hydrogenated for 16 hours, then filtered through decalite. Solvent is removed to afford 7,8-dimethoxy-3,4-dihydro-1H-quinoxalin-2-one as an off-white solid (0.46 g, 52% yield).

Workup

  1. filtrationfiltered through decalite
  2. customSolvent is removed

Sources & evidence

ORD record
ord-250f49e489944bbc9656a9153e512cd0
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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