Water → 5-Hydroxypyridine-3-carbonitrile

HRID 334412Notes

Reaction equation

HRID 334412 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-1a14881e0a124b9dbf8f7a491c553bf3
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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