Piperidine → Isonicotinic Acid

HRID 261723Notes

Reaction equation

HRID 261723 reaction equation
[CH:1]([O:3]C1C=CN=CC=1)=[O:2].[C]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(=O)(O)[O-].[Ni+2].C(=O)(O)[O-].I([O-])(=O)=O.[Mg+2].I([O-])(=O)=O>[N:12]1[CH:17]=[CH:16][C:15]([C:1]([OH:3])=[O:2])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 19791021HCID 19791021, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 5922Isonicotinic Acid

Reagents, catalysts & solvents 2

HCID 165645Iodic acid (HIO3), magnesium salt (2:1)CatalystHCID 13644056Carbonic acid, nickel(2+) salt (2:1)Catalyst

Procedure

A 100-ml. inner capacity stainless steel autoclave of a shaker type is charged with 22.0 grams (0.179 mol) of 4-pyridyl formate. Further piperidine of 1.0 mol as solvent and nickel bicarbonate of 0.045 mol and magnesium iodate of 0.050 mol as catalyst, are added thereto per mol of starting formic acid ester. Carbon monoxide is introduced into the autoclave under pressure. The reaction is conducted for 2.0 hours at 260° C. and 500 kg./cm.2 gauge. After termination of the reaction, the autoclave is cooled and the reaction product is taken away therefrom. The unreacted 4-pyridyl formate is distilled off. Further distillation of the remaining liquor gives pyridine-4-carboxylic acid in a yield of 4.43 grams (0.036 mol) corresponding to a conversion of 20.1% based on the starting formic acid ester.

Workup

  1. customAfter termination of the reaction
  2. temperaturethe autoclave is cooled
  3. distillationThe unreacted 4-pyridyl formate is distilled off
  4. distillationFurther distillation of the remaining liquor

Sources & evidence

ORD record
ord-e15d31e6352f4d41a3fa375f44e3f5bd
Source dataset
uspto-grants-1979_05
Patent number
USRE029981

Reaction notes

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