Pyridine → Cyanide

HRID 423204Notes

Reaction equation

HRID 423204 reaction equation
[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

Participants

4

Reactant 2

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

Product 2

HCID 5975CyanideHCID 8176943-Bromopyridine-2-carbonitrile

Procedure

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).

Sources & evidence

ORD record
ord-c8f672f6d4f647e28fd68e3159101be2
Source dataset
uspto-grants-2012_01
Patent number
US08101760B2

Reaction notes

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