Pyridine → 1-(Pyridin-4-yl)pyridin-1-ium chloride--hydrogen chloride (1/1/1)

HRID 495676Notes

Reaction equation

HRID 495676 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:9])=O>C(OCC)(=O)C>[ClH:9].[Cl-:9].[N:1]1[CH:6]=[CH:5][C:4]([N+:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 24386Thionyl Chloride

Product 1

HCID 794611-(Pyridin-4-yl)pyridin-1-ium chloride--hydrogen chloride (1/1/1)

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

In another aspect, the present invention is directed to an improved process for producing 4-dimethyl amino pyridine that provides for the recovery of ethyl acetate during salt formation and recycling the ethyl acetate. The process comprises quaternizing pyridine with thionyl chloride in presence of recovered ethyl acetate to provide N-[4-pyridyl]pyridinium chloride hydrochloride and then aminating the resulting salt with N,N-dimethyl formamide. The resulting reaction mass is hydrolysed in presence of a base, extracted with an aromatic solvent, such as benzene, and distilled under vacuum employing a fractionating column to give 4-dimethyl amino pyridine with the desired quality and yield.

Sources & evidence

ORD record
ord-0e5a626de4c7433c9eba9220bb5e21a6
Source dataset
uspto-grants-2005_09
Patent number
US06939972B2

Reaction notes

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