Diethyl Carbonate → 2-(4-Chloro-2-pyridinyl)acetamide

Temperature

-70 °C

A solution of 4-chloro-2-methylpyridine (1.28 g) in diethyl ether (15 ml) was treated at −70° C. dropwise with a 2M lithium diisopropylamide heptane/THF solution (6.0 ml) and stirred at −70° C. for 30 minutes. The mixture was treated dropwise also with diethyl carbonate (1.45 ml) at −70° C., and stirred at −70° C. for 1 hour. The reaction mixture was allowed to warm to room temperature, and combined with aqueous sodium bicarbonate and dichloromethane, and the organic phase was isolated, dried and concentrated. A mixture of the resultant residue and a 13% solution of ammonia in methanol (5 ml) was stirred at 75° C. for 7 hours. The reaction mixture was concentrated, and the resultant residue was triturated from diethylether to obtain the title compound (0.47 g) as a tan powder.

1. stirringstirred at −70° C. for 1 hour
2. temperatureto warm to room temperature
3. customthe organic phase was isolated
4. customdried
5. concentrationconcentrated
6. additionA mixture of the resultant residue
7. stirringa 13% solution of ammonia in methanol (5 ml) was stirred at 75° C. for 7 hours
8. concentrationThe reaction mixture was concentrated
9. customthe resultant residue was triturated from diethylether

ORD record

ord-2cf8633ca49c410ca528570b228a5385

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723722B1