Water → 5-Hydroxypyridine-3-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe crude reaction product
- extractionextracted again with diethyl ether
- customThe organic phase is dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ec81dfba4db14ae28f27aa67adb83800
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09381195B2
Reaction notes
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