5-Fluoro-2-nitrobenzoic acid → 2-Amino-5-fluorobenzoic acid

HRID 1767491Notes

Reaction equation

HRID 1767491 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>C(O)C.[Pd]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 1014122-Amino-5-fluorobenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Compound 33 (10 g, 54 mmol) in ethanol (100 mL) was stirred under hydrogen in the presence of 10% Pd/C (0.5 g) at room temperature for 4 h. The solution was filtered through celite. The solvent was evaporated under reduced pressure to yield 8.2 g (98%) of white solids. M.P. 142° C. 1H NMR (DMSO-d6): 6.71 (dd, J=4.9, 8.9 Hz, 1H), 7.15 (dt, J=2.9, 8.4 Hz, 1H), 7.37 (dd, J=2.9, 9.8 Hz, 1H), 8.60 (s, 1H). EIMS m/z 156 (M+1).

Workup

  1. filtrationThe solution was filtered through celite
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6c81642042a44e5aac0709f6116b1606
Source dataset
uspto-grants-2007_06
Patent number
US07235546B2

Reaction notes

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