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

HRID 1702140Notes

Reaction equation

HRID 1702140 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 acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

One hundred eleven g of 2-fluoro-5-nitrobenzoic acid was dissloved 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, then evaporated to dryness to provide a tan residue of 95.2 g of 5-amino-2-fluorobenzoic acid.

Workup

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

Sources & evidence

ORD record
ord-3f6b1270e542499996903cc39bfee87e
Source dataset
uspto-grants-1983_04
Patent number
US04380543

Reaction notes

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