Hydrochloric Acid → 5-Formylpyridine-2-carbonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2OCC[O:10]2)=[CH:5][N:4]=1)#[N:2].Cl>O1CCCC1>[C:1]([C:3]1[N:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][CH:8]=1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-Cyano-5-(1,3-dioxolan-2-yl)pyridine (478 mg, 2.71 mmol) was dissolved in tetrahydrofuran (5.0 mL). To this, 1N hydrochloric acid (5.0 mL) was added under a nitrogen atmosphere at room temperature and the mixture was stirred at the same temperature for 16 hours and successively at 50° C. for 13 hours. Then, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and thereby 6-cyano-3-pyridinecarboxaldehyde (364 mg, yield: 100%) was obtained.
Workup
- extractionThen, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate
- washby washing with brine
- dry with materialdrying over anhydrous sodium sulfate
- customThe solvent was evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-8e883f486bea4b92aa932339584784b8
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673908B2
Reaction notes
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