2-Fluoro-3-nitrobenzoic acid → 3-Amino-2-fluorobenzoic acid

HRID 1187300Notes

Reaction equation

HRID 1187300 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>CO.[Pd]>[NH2:11][C:10]1[C:2]([F:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 186729922-Fluoro-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 230943433-Amino-2-fluorobenzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-fluoro-3-nitro-benzoic acid (70, 6.77 g, 36.6 mmol) in 150 mL of methanol, Palladium on carbon (5:95 Palladium:Carbon, 0.338 g, 0.159 mmol) is added under a balloon of hydrogen. The reaction is stirred at room temperature for 40 hours, then a new balloon of hydrogen is attached, and the reaction continued for 5 hours. The reaction is filtered and the filtrate is concentrated under vacuum to provide the desired compound (71, 5.62 g). MS (ESI) [M−H+]−=154.1.

Workup

  1. waitthe reaction continued for 5 hours
  2. filtrationThe reaction is filtered
  3. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-72bd47c0561741b980527bc2e8962afb
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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