2-Nitro-4-(trifluoromethyl)benzoic acid → 4-(Trifluoromethyl)anthranilic acid

HRID 491922Notes

Reaction equation

HRID 491922 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.[H][H]>CCO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 6420962-Nitro-4-(trifluoromethyl)benzoic acidHCID 178418361HCID 178418361, compound3×

Product 1

HCID 678694-(Trifluoromethyl)anthranilic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

250 g of 2-nitro-4-trifluoromethylbenzoic acid (1.06 mol) were dissolved in 1 l of EtOH and 7.5 g of Pd/C (5%) were added. The mixture was hydrogenated under 1-2.5 bar of hydrogen pressure. During the hydrogen uptake, the temperature rose temporarily from 10° C. to 104° C. After 2 h, the hydrogen uptake was complete. Subsequently, the catalyst was filtered off and the solvent was removed under reduced pressure to obtain 215 g (99%) of a pale yellow solid, mp 174-176° C.

Workup

  1. customrose temporarily from 10° C. to 104° C
  2. filtrationSubsequently, the catalyst was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-83ea1430b3ed4707bbf99aa2b835e60f
Source dataset
uspto-grants-2009_05
Patent number
US07531569B2

Reaction notes

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