Sulfuric Acid → 5-Hydroxypyridine-2-carbonitrile
Reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:10]S(O)(=O)=O.N([O-])=O.[Na+]>O>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:10])=[CH:7][N:6]=1)#[N:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 100 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 5-amino-2-cyano pyridine (1.0 g, 8.38 mmol), conc. H2SO4 (4.2 mL), water (15 mL) and the mixture was cooled to 0° C. A solution of NaNO2 (636 mg, 9.22 mmol) in water (5.7 mL) was added slowly at 0° C. Then the reaction mixture was stirred for 30 min at 0° C. The reaction mixture was poured into a boiling mixture of water (11 mL) and H2SO4 (1 mL) and stirred for 30 min. The mixture was cooled and extracted with EtOAc. The organic layer was washed with water, dried and concentrated to give 2-cyano-5-hydroxy pyridine (900 mg, 89%).
Workup
- customIn a 100 mL round-bottomed flask fitted with condenser and magnetic stirrer
- stirringstirred for 30 min
- temperatureThe mixture was cooled
- extractionextracted with EtOAc
- washThe organic layer was washed with water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f93ca973f5274b91851dc8c302b98bba
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093273B2
Reaction notes
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