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

HRID 270231

Reaction equation

HRID 270231 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>CO.[Pd]>[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

4

Reactant 1

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 6095563-Amino-5-(trifluoromethyl)benzoic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-nitro-5-(trifluoromethyl)benzoic acid (5.4 g, 23 mmol) in MeOH (115 mL) was charged with 5% Pd/C, Degussa (1.09 g). The reaction vessel was purged with hydrogen and stirred under a hydrogen atmosphere (1 atm) for 3 h. The mixture was filtered and the filtrate was concentrated in vacuo to provide 3-amino-5-(trifluoromethyl)benzoic acid (4.25 g). This material was incorporated into procedure (80a) to provide 3-benzylamino-5-(trifluoromethyl)benzoic acid, a portion (17 mg, 0.06 mmol) of which was incorporated into procedure (91b). Purification by RP-HPLC afforded the title compound (S)-1.5 (R1=2,4-dimethylphenyl, R3=—C(O)NHt-Bu, Z=—C(O)—, R2=3-benzylamino-5-(trifluoromethyl)phenyl, all other R=H; 3 mg). Exact MS calcd for C33H41F3N5O3, the formula for (M+H)+=612.3161. Found: 612.3184.

Workup

  1. customThe reaction vessel was purged with hydrogen
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee15a0e0b1374d3d83a467ed0abf52ee
Source dataset
uspto-grants-2008_11
Patent number
US07449493B2

Linked notes

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