Reaction #710478

Reaction equation

2-aminopyridine

EDC-HCl

pentafluoropropionic acid

→

2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide

Yield 11.1%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washwashed once with water and twice with 1% hydrochloric acid
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

300 mg (3.19 mmol) of 2-aminopyridine was dissolved in 15 ml of anhydrous dichloromethane, 919 mg (4.78 mmol) of EDC-HCl, 583 mg (4.78 mmol) of DMAP and 397 μl (628 mg, 3.83 mmol) of pentafluoropropionic acid were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 85 mg (yield 11%) of 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide.

Source