Thionyl Chloride → 4-Chlorocarbonyl-2-nitrobenzyl isonicotinate hydrochloride

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Reaction Steps

The 4-carboxy-2-nitrobenzyl isonicotinate (C) was treated with excess thionyl chloride and a few drops of dimethylformamide at room temperature for 45 minutes, followed by rotary evaporation to remove thionyl chloride and azeotropic removal of thionyl chloride by 3 additions of toluene followed by rotary evaporation to give 4-chlorocarbonyl-2-nitrobenzyl isonicotinate hydrochloride (D). The 4-chlorocarbonyl-2-nitrobenzyl isonicotinate hydrochloride (D) and excess triethylamine were dissolved in chloroform and cooled in an ice/acetone bath. A chloroform solution of 3-aminopropyltriethoxysilane was added dropwise and the reaction was allowed to warm to room temperature and stirred for 4 hours. The solvents were removed by rotary evaporation. The resultant mixture was treated with ether and filtered to remove salts. The filtrate was rotary evaporated and purified by flash chromatography on silica gel using ethyl acetate as the eluent to yield 4-[N-(3-triethoxysilyl)propyl]carbamoyl-2-nitrobenzyl isonicotinate.

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