ChemicalBook CAS DataBase List N-(3-FORMYL-4-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE

N-(3-FORMYL-4-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE synthesis

4synthesis methods

Product Name:N-(3-FORMYL-4-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE
CAS Number:86847-71-4
Molecular formula:C11H14N2O2
Molecular Weight:206.24

70298-89-4 Synthesis

2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE

70298-89-4
126 suppliers
$6.00/250mg

N-(3-FORMYL-4-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE

86847-71-4
66 suppliers
$15.00/100mg

Yield:86847-71-4 69%

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;methanol;N,N-dimethyl-formamide;

Steps:

25.B N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamide

Example 25B N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamide A mixture of Example 25A (11.4 g, 64 mmol) in 200 mL THF was cooled to -78° C., treated with 1.6 M nBuLi in hexanes (100 mL, 160 mmol), warmed to ⁰° C., stirred for 1 hour, treated with a solution of DMF (22 g, 215 mmol) in 100 mL THF, warmed to room temperature, stirred for 1 hour, diluted with brine, and extracted three times with ethyl acetate. The combined extracts were washed with water, washed twice with brine, dried (MgSO₄), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane to provide the desired product (9.1 g, 69%).

References:

US2003/187026,2003,A1