Iodine → 4,4'-Bipyridine

HRID 236883

Reaction equation

HRID 236883 reaction equation
[Cl-].[NH+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:8]#[N:9].[Na+].II.[OH-].[Na+]>O.CC(C)=O>[N:2]1[CH:7]=[CH:6][C:5]([C:4]2[CH:5]=[CH:6][N:9]=[CH:8][CH:3]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 69401Einecs 211-027-4

Product 1

HCID 111074,4'-Bipyridine

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To 22 parts of 1-[2-pyridyl)ethyl] pyridinium chloride (obtained from pyridine and 2-vinylpyridine as in Example 13) in 100 parts of a mixture of water-acetone (1:1 v/v) was added five parts sodium cyanide, and the mixture stirred 24 hours at 25° C. The resulting dark blue solution was oxidized with an alcoholic iodine solution until the blue color disappeared and 100 parts 40% sodium hydroxide added. Cleavage of the quat and workup as in Example 15 gave 4.9 parts 4,4'-bipyridine.

Sources & evidence

ORD record
ord-8f40871ea4d94657a6ba8d140964d24f
Source dataset
uspto-grants-1979_06
Patent number
US04158093

Linked notes

Loading…