(2-Fluoro-6-nitrophenylamino)acetic acid ethyl ester → 5-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

HRID 558941Notes

Reaction equation

HRID 558941 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:8]=1[F:16])C>CO.[Pd]>[F:16][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][CH2:5][C:4](=[O:3])[NH:13]2

Participants

4

Reactant 1

HCID 67000141(2-Fluoro-6-nitrophenylamino)acetic acid ethyl ester

Product 1

HCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of (2-fluoro-6-nitrophenylamino)acetic acid ethyl ester from Example B2 (2.1 g, 8.7 mmol) in methanol (65 ml) was added palladium on carbon (10%, 600 mg). Hydrogen gas was bubbled through the mixture for 75 mins, filtered through Celite® and reduced in vacuo. The residues was purified by flash chromatography on silica (eluant EtOAc: pet. ether 50:50); yield 1.02 g, 71%.

Workup

  1. customHydrogen gas was bubbled through the mixture for 75 mins
  2. filtrationfiltered through Celite®
  3. customThe residues was purified by flash chromatography on silica (eluant EtOAc: pet. ether 50:50)

Sources & evidence

ORD record
ord-2bf0be37b7da4756bd9fb922566b27a2
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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