Pyridine → Cyanide

HRID 423204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423204
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[N:9]1C=CC=C[CH:10]=1>>[C-:3]#[N:4].[Br:1][C:2]1[C:3]([C:10]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 1049PyridineHCID 142763Pyridine, 3-bromo-, 1-oxide

Produkt 2

HCID 5975CyanideHCID 8176943-Bromopyridine-2-carbonitrile

Versuchsvorschrift

In Scheme I is described the preparation of pyridine intermediates (5), (6), and (7). In Scheme I, Step 1,3-bromopyridine (1) is oxidized to 3-bromo-pyridine-N-oxide (2). In Scheme I, Step 2, cyanide substitution gives 3-bromo-pyridine-2-carbonitrile (3). The nitrile of formula (3) is hydrolyzed in Step 3 to the carboxylic acid and esterified with acid catalysis to the ester of formula (4). In Scheme I, Step 4, the ester is reduced to the pyridinylmethanol of formula (5) using sodium borohydride. The pyridinylmethanol is converted to the mesylate of formula (6) with methanesulfonyl chloride (Step 5) or to the pyridinylmethyl chloride of formula (7) using thionyl chloride (Step 6).

Quellen und Nachweise

ORD-Eintrag
ord-c8f672f6d4f647e28fd68e3159101be2
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101760B2

Notizen zur Reaktion

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