4-Fluoro-3-nitrobenzoic acid → 3-Amino-4-fluorobenzoic acid

HRID 1515513Notes

Reaction equation

HRID 1515513 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.[H][H]>CO.[Pd]>[NH2:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[F:1])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 753963-Amino-4-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Fluoro-3-nitrobenzoic acid (270 mg, 2 mmol) and 10% Pd/C (80 mg) in MeOH (10 mL) was hydrogenated with a hydrogen balloon for 6.0 h. LC-MS indicated a completion of reaction. The mixture was filtered and the filtrate was concentrated to give 19A. 1H NMR (400 MHz, CDOD3) δ ppm 7.00 (dd, J=10.99, 8.79 Hz, 1H) 7.27-7.36 (m, 1H) 7.49 (dd, J=8.79, 2.20 Hz, 1H).

Workup

  1. customa completion of reaction
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-63c5009c02b94783a540e1011f4b2cb8
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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