HCID 10375029, compound → 3-Hydroxy-4-methyl-2-pyridinecarboxaldehyde
Reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:11](N)=[C:10]([CH3:13])[CH:9]=[CH:8][N:7]=1.N([O-])=[O:15].[Na+]>OS(O)(=O)=O.O>[OH:15][C:11]1[C:6]([CH:2]=[O:1])=[N:7][CH:8]=[CH:9][C:10]=1[CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(1,3-dioxolanyl)-4-methyl-3-aminopyridine (0.60 g, 3.3 mmol) in 15 mL of 10% H2SO4 at 0° C. (ice bath) with stirring was added dropwise a solution of NaNO2 (0.38 g, 5.5 mmol) in 3 mL of water. The mixture was stirred at 0° C. for 15 min and then heated in a steam-bath for 30 min. The resulting solution was evaporated at room temperature under reduced pressure to yield 3-hydroxy-4-methyl-2-formylpyridine as a syrup, which was dissolved in 15 mL of water, decolorized with charcoal and filtered. To the filtrate was added a solution of thiosemicarbazide (0.31 g, 3.3 mmol) in 5 mL of 5% HCl. The mixture was refluxed for 30 min, cooled and the yellow precipitate was filtered, washed with water, and recrystallized from aqueous ethanol solution (1:1, v/v) containing 5% conc. HCl to afford 0.21 g (30%) of product: the mp and all spectroscopic data were identical with those obtained in Example XLIII.
Workup
- temperatureheated in a steam-bath for 30 min
- customThe resulting solution was evaporated at room temperature under reduced pressure
Sources & evidence
- ORD record
- ord-6188146fde554b90975cdc3fd202d387
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05281715
Reaction notes
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