Methyl 2-amino-5-fluoro-3-nitrobenzoate → 2,3-Diamino-5-fluoro-benzoic acid methyl ester

HRID 1470594Notes

Reaction equation

HRID 1470594 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[NH2:14].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[NH2:14]

Participants

5

Reactant 2

HCID 20577070Methyl 2-amino-5-fluoro-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 580739282,3-Diamino-5-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 2-amino-5-fluoro-3-nitro-benzoic acid methyl ester (1.8 g, 84.0 mmol) and 10% Pd/C (0.5 g) in methanol (50 mL) was hydrogenated with a hydrogen balloon for 2 h. After completion of the reaction, the reaction mixture was filtered over celite bed, concentrated to dryness. the resulting residue was purified by column chromatography using 30% ethyl acetate in hexane to obtain the title compound as off white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered over celite bed
  3. concentrationconcentrated to dryness
  4. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-6e2d34443e934eb7bccee01766424ab7
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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