4-Aminopyridine → 2-chloro-N-(pyridin-4-yl)acetamide

Temperature

0 °C

A suspension of 4-aminopyridine (0.96 g) in dry dichloromethane (10 mL) under nitrogen was cooled to 0° C. in an ice bath. Triethylamine (1.56 mL) was added, followed by the slow addition of chloroacetyl chloride (0.89 mL). The ice bath was removed and the reaction mixture allowed to reach room temperature. The reaction mixture was diluted with water (20 mL) and dichloromethane (25 mL). The solid was filtered off, washed with pentane and dried to give the title compound as a brown solid (0.87 g). The layers of the filtrate were separated and the organic layer was washed with water, dried and the solvent was evaporated to give a dark brown glass. Trituration with pentane gave another batch of the title compound (0.91 g).

1. customThe ice bath was removed
2. customto reach room temperature
3. additionThe reaction mixture was diluted with water (20 mL) and dichloromethane (25 mL)
4. filtrationThe solid was filtered off
5. washwashed with pentane
6. customdried

ORD record

ord-19f2a55b57ff43a2a5951729eae1cfca

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329729B2