Ethyl 3-nitro-4-(trifluoromethyl)benzoate → Ethyl 3-amino-4-(trifluoromethyl)benzoate

HRID 257576

Reaktionsgleichung

Reaktionsgleichung von HRID 257576
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O.[H][H]>[Pt]=O.C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[C:15]([F:16])([F:17])[F:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 2

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 19783159Ethyl 3-amino-4-(trifluoromethyl)benzoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 395 mg (1.50 mmol) of ethyl 3-nitro-4-(trifluoromethyl)benzoate (from Step C), 20 mg of platinum oxide, and 6 mL of ethanol was shaken with hydrogen at 3-4 atm. for a few hours, by which time the reaction was essentially complete. The catalyst was removed by filtration, and the filtrate was concentrated to dryness. The residue was chromatographed on silica gel (elution with 25:1 hexane-EtOAc) to afford a 77% yield of the title compound as a pale yellow, gummy foam; TLC in 4:1 hexane-EtOAc; mass spectrum (EI) m/e 233 (M+). 200 MHz 1H NMR (CD3OD) δ1.36 (t, J=7.1 Hz, 3H), 4.33 (q, J=7.1 Hz, 2H), 7.26 (d, J=8 Hz, 1H), 7.44 (d, J=8 Hz, 1H) overlapping 7.47 (s, 1H).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was chromatographed on silica gel (elution with 25:1 hexane-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b86ff7fc4ddb4d5a9165de3656719aa1
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262412

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