Sodium Iodide → 6-Iodopyridine-3-carboxylic acid

To 27.97 g (186.6 mmol) of sodium iodide cooled to -78° C. was added 121.77 g (71.6 ml, 952.0 mmol) of hydriodic acid (57 wt %). The reaction mixture was allowed to warm slightly with stirring for 5 minutes, and then 30.00 g (190.4 mmol) of 6-chloronicotinic acid was added. The resulting mixture was allowed to warm to room temperature with stirring and then heated at 120°-125° C. in an oil bath for 42 hours. A dark brown layer formed above the yellow solid material. The reaction mixture was allowed to cool to room temperature and then poured into acetone (chilled to 0° C.). The resultant yellow solid was collected by filtration, washed with 200 ml of 1N NaHSO3 solution, and dried in high vacuum (3 mm Hg) to give the title compound as a pale yellow solid.

1. temperatureto warm slightly
2. stirringwith stirring
3. temperatureheated at 120°-125° C. in an oil bath for 42 hours
4. customA dark brown layer formed above the yellow solid material
5. temperatureto cool to room temperature
6. filtrationThe resultant yellow solid was collected by filtration
7. washwashed with 200 ml of 1N NaHSO3 solution
8. customdried in high vacuum (3 mm Hg)

ORD record

ord-03dbd1f43cac4382b3dd1b2085cef513

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591858