4-Pyridinecarbonitrile,2-formyl-(9CI)
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4-Pyridinecarbonitrile,2-formyl-(9CI)
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CAS No:
116308-38-4
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Formula:
C7H4N2O
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Chemical Name:
4-Pyridinecarbonitrile,2-formyl-(9CI)
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Synonyms:
4-Pyridinecarbonitrile,2-formyl-(9CI);4-Cyanopyridine-2-carboxaldehyde;2-forMyl-4-pyridinecarbonitrile;2-forMylisonicotinonitrile;2-Formylpyridine-4-carbonitrile;4-Cyano-2-pyridinecarboxaldehyde
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CAS No:
4-Pyridinecarbonitrile,2-formyl-(9CI) Use and Manufacturing
To a cooled solution of oxalyl chloride (13.2mL, 150mmol) in anhydrous DCM (86mL) under nitrogen atmosphere at -78°C was added DMSO (21.2ml_ dropwise over 20 minutes. The mixture was stirred for 15 minutes at (-78°C) before 2-hydroxymethyl-isonicotinonitrile (4.0g, 30 mmol) dissolved in anhydrous DCM (60mL) was added dropwise to the reaction mixture over 5 minutes. The reaction was stirred for 2 hrs at -78°C maintaining a nitrogen atmosphere. A white solid precipitate formed and the temperature was raised to (-55°C) and triethylamine (6.15mL, 450mmol) was added dropwise for over 15 minutes, cooling bath was removed allowing the mixture to warm to room temperature over 2 hrs. The mixture was diluted with DCM (400ml_) and washed with brine (2x 50mL). The aqueous phase was extracted with DCM (3x 50 ml_). The combined organic layers were combined and concentrated in vacuo. A buff white solid was isolated that was used without any further purification. Single peak in LC-MS analysis, (yield taken to be quantitative), m/z (LC-MS, ESP), RT=2.53mins, (M+H)=133.0.General procedure: The E isomer of hydrazones 1-15 all can be easily to get by similar procedures. The corresponding aldehydes and hydrazine hydrochloride were added to the methanol solution, then the reaction mixture was heated under reflux for 10 h. After the reaction was finished, removed the solvent in vacuo. The residue was dissolved in water and neutralized with saturated NaHCO3 solution. Afterwards, extracted with dichloromethane and collected the organic layer. The organic layer were dried over by Na2SO4, filtered and concentrated. The residue was recrystallized by methanol to give the pure product.
Computed Properties
Molecular Weight:132.12
XLogP3:0.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:132.032362755
Monoisotopic Mass:132.032362755
Topological Polar Surface Area:53.8
Heavy Atom Count:10
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Pyridinecarbonitrile,2-formyl-(9CI)
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