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

HRID 1285208Notes

Reaction equation

HRID 1285208 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 2809972-Fluoro-5-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 27359105-Amino-2-fluorobenzoic acidYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

One hundred eleven g of the above 2-fluoro-5-nitrobenzoic acid (0.60 mole) was dissolved in 1 liter of ethyl acetate. To this solution was added 5 g of 5 percent palladium on charcoal. The mixture was hydrogenated on a Parr apparatus for 24 hours at 20° C. at 50 psi of hydrogen. The theoretical amount of hydrogen was absorbed. The solution was filtered and evaporated to dryness to provide a tan residue of 95.2 g of 5-amino-2-fluorobenzoic acid, a known compound.

Workup

  1. customThe theoretical amount of hydrogen was absorbed
  2. filtrationThe solution was filtered
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-336726a0cd0644cd849d87efb4ab74d6
Source dataset
uspto-grants-1986_01
Patent number
US04565872

Reaction notes

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