Nicotinoyl chloride hydrochloride

Chemical Properties

white to off-white crystalline powder

Uses

Nicotinoyl chloride hydrochloride was used in the preparation of :

• 1-[5-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-3-O-(3-pyridylcarbonyl)-β-D-ribofuranosyl]uracil
• 7,16-dinicotinoylated and/or 7,16-diisonicotinoylated compounds via reaction with tetraaza[14]annulene and its complexes
• bis(ethylenedithio)tetrathiafulvalene derivatives

Uses

Nicotinoyl chloride hydrochloride was used in the preparation of 1-[5-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-3-O-(3-pyridylcarbonyl)-β-D-ribofuranosyl]uracil, bis(ethylenedithio)tetrathiafulvalene derivatives and 7,16-dinicotinoylated or 7,16-diisonicotinoylated compounds via reaction with tetraaza[14]annulene and its complexes.

Uses

As a Nicotinic Acid analog, Nicotinoyl chloride hydrochloride can be used in the preparation of cardiovascular agents and renal drugs.

Synthesis

Niacin (8.12 mmol) and 2 drops of anhydrous DMF were added to SOCl2 (10 mL) under anhydrous conditions with vigorous stirring at 0°C. The reaction mixture was heated to 78 °C and refluxed for 3 hours. Upon completion of the reaction, the excess SOCl2 was removed by evaporation under reduced pressure to give a yellow solid. Subsequently, 10 mL of diethyl ether was added to the solid and refluxed for 1 hour. The reaction mixture was filtered to give a white solid nicotinoyl chloride hydrochloride in a yield of 1.388 g (yield: 96.0%).

References

[1] Dalton Transactions, 2005, # 3, p. 424 - 426
[2] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6691 - 6702
[3] Green Chemistry, 2009, vol. 11, # 1, p. 83 - 90
[4] Molecules, 2014, vol. 19, # 4, p. 4791 - 4801
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 3, p. 552 - 557