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

HRID 1690023Notes

Reaction equation

HRID 1690023 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]>O1CCCC1.[OH-].[OH-].[Pd+2]>[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

4

Reactant 1

HCID 186729922-Fluoro-3-nitrobenzoic acid

Product 1

HCID 230943433-Amino-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluoro-3-nitro-benzoic acid (28, 2.0 g, 11 mmol) in 45 mL of tetrahydrofuran, 20% palladium hydroxide on carbon (150 mg) was added. The reaction was stirred under hydrogen for 2 hours, then filtered and the filtrate concentrated under vacuum to provide the desired compound 29 as a white solid, which was used in the next step without further purification. MS(ESI) [M−H+]−=154.4.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-b469ed2837a74e2d84f690c3ebfe3772
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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