4-Bromobutyronitrile → Methylanabasine

HRID 27252

Reaktionsgleichung

Reaktionsgleichung von HRID 27252
[CH3:1][C:2]1[C:7]([CH:8](C#N)[CH2:9][CH2:10][C:11]([CH2:13]CC(C#N)C2C(C)=NC=CC=2)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(CCC(C1C(C)=NC=CC=1)=O)#[N:28].BrCCCC#N>N.[Ni]>[CH3:1][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]1[NH:28][CH2:13][CH2:11][CH2:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 214124-BromobutyronitrileHCID 122824282-Methyl-3-pyridyl 2-cyanoethyl ketoneHCID 705534922-Methyl-3-pyridyl-3-cyanopropyl ketone

Produkt 1

HCID 3053192MethylanabasineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittel

Versuchsvorschrift

The preparation of 2-methyl-3-pyridyl-3-cyanopropyl ketone was carried out using the procedure described for the synthesis of 2-methyl-3-pyridyl 2-cyanomethyl ketone (Preparation III) except that 4-bromobutyronitrile was used instead of 3 bromopiopionitrile. A solution of 2.8 g of the ketone in 150 ml ammonia saturated ethanol was prepared and 10 g of freshly prepared Raney nickel was added. The mixture was hydrogenated for 20 hours in a Parr apparatus at 67 psi. The reaction mixture was worked up as in Example 2. The product was isolated by distillation (108°-112°/0.2 mm Hg) to give 2.2 g (89%) of 2-methylanabasine.

Aufarbeitung

  1. customThe product was isolated by distillation (108°-112°/0.2 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-b1b24ed8837545f4abf5b464bdc6fe64
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220781

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