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

HRID 488943

Reaktionsgleichung

Reaktionsgleichung von HRID 488943
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 6095563-Amino-5-(trifluoromethyl)benzoic acidAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-70e31666ebd54a948b11062abaae5666
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974836B2

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