3-Nitro-5-(trifluoromethyl)benzoic acid → 3-Amino-5-(trifluoromethyl)benzoic acid

HRID 1441757Notes

Reaction equation

HRID 1441757 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 6095563-Amino-5-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-nitro-5-(trifluoromethyl)benzoic acid (Lancaster Synthesis GmbH; 11.75 g, 50 mmol) in ethanol (300 mL) is hydrogenated at atmospheric pressure over Raney nickel (1 g) at 40° C. The calculated amount of hydrogen is taken up after 8 hours. The mixture is then filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from diethylether-hexane to give the title compound as a beige crystalline solid, m.p. 134-139° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customthe solvent is evaporated off under reduced pressure
  3. customto yield the crude product which
  4. customis purified by recrystallisation from diethylether-hexane

Sources & evidence

ORD record
ord-a470078fe6ba497fbca2b0aebfe76741
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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