Toluene → Isopropyl 5-chloro-6-isopropoxynicotinate

Participants

Reaction Steps

The 5-chloro-6-hydroxy-3-pyridinecarboxylic acid (1 g, 5.76 mmol) was suspended in toluene (200 ml) and treated with silver carbonate (3.97 g, 14.40 mmol) and 2-iodopropane (3.46 ml, 34.6 mmol) and stirred at RT in the dark for 3 days. LC/MS showed 2/3 product. Added 2-iodopropane (3 ml) and stirred for 24 hours. LC/MS showed 80% product. Added EtOAc (200 ml) and washed with water (200 ml)+sat. NaHCO3 (50 ml) followed by water (200 ml). Dried over MgSO4 and evaporated off the solvent to yield 1.0 g of the title compound as a clear, colourless oil. MS (ES+) C12H1635ClNO3 requires 257; found 257.

Provenance & Evidence