4-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile → [4-Methanesulfonyl-3-(trifluoromethyl)phenyl]methanamine

HRID 1364555

Reaktionsgleichung

Reaktionsgleichung von HRID 1364555
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])(=[O:4])=[O:3]>N.CO.[Ni]>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][C:6]=1[C:13]([F:14])([F:15])[F:16])(=[O:4])=[O:3]

Komponenten

5

Edukt 1

HCID 459337164-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile

Produkt 1

HCID 66632608[4-Methanesulfonyl-3-(trifluoromethyl)phenyl]methanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

Aufarbeitung

  1. customfor 2 h
  2. filtrationThe reaction mixture was filtered through a celite plug
  3. washwashed with methanol
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f6a0f34fb0a64f62a97a309ec3886341
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888374B2

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