Water → 5-Hydroxypyridine-3-carbonitrile

HRID 1487383Notes

Reaction equation

HRID 1487383 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:10]=1)[C:8]#[N:9].Cl.N1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>C(OCC)C>[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 231597785-Methoxypyridine-3-carbonitrile

Product 1

HCID 153421425-Hydroxypyridine-3-carbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1 g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200° C. for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95%) in the form of a beige solid.

Workup

  1. customThe crude reaction product
  2. extractionextracted again with diethyl ether
  3. customThe organic phase is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c391eaa1f5f4aff821b29aefc68cd20
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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