Ethanol → Ethyl6-iodonicotinoate

Temperature

50 °C

To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed once with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to yield a yellow solid residue. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white solid. PMR (CDCl3): d 1.41 (3H, t, J=7.1 Hz), 4.41 (2H, q, J=7.1 Hz), 7.85 (1H, d, J=8.2 Hz), 7.91 (1H, dd, J=8.2, 2.1 Hz), 8.94 (1H, d, J=2.1 Hz).

1. concentrationconcentrated in vacuo
2. custompartitioned between 200 ml of water and 250 ml of ethyl ether
3. customthe layers were separated
4. washThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
5. washwashed once with 75 ml of brine solution
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto yield a yellow solid residue
10. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

ORD record

ord-5a55b4eba1f849c5a736fa289233e068

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369100B1