HCID 19361727, compound → 6-(Dimethylamino)pyridine-2-carbaldehyde
Reaction equation
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][CH:7]=1>C(O)=O>[CH3:13][N:12]([CH3:14])[C:10]1[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
0.60 g of (6-[1,3]dioxolan-2-yl-pyridin-2-yl)dimethylamine (3.09 mmol) is mixed in 10 ml of an aqueous solution of formic acid at 80% and then the solution is heated at 60° C. for 20 hours. The solvents are removed by azeotropic entrainment with toluene, the residue is taken up in water, the mixture is cooled to 0° C. and then the medium is basified by addition of potassium carbonate. The mixture is extracted with ethyl acetate, the organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered, and the solvent is evaporated under vacuum. The title product is obtained in the form of a yellow oil (0.43 g) which is used in the next stage without further purification.
Workup
- customThe solvents are removed by azeotropic entrainment with toluene
- temperaturethe mixture is cooled to 0° C.
- additionthe medium is basified by addition of potassium carbonate
- extractionThe mixture is extracted with ethyl acetate
- washthe organic phase is washed with water
- dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
- filtrationfiltered
- customthe solvent is evaporated under vacuum
Sources & evidence
- ORD record
- ord-edd6a7625ae64fe2b2419730173bbda0
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06020345
Reaction notes
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