Reaction #62214

Reaction equation

4-Aminopyridine

p-anisoyl chloride

triethylamine

→

colorless solid

Yield 81.0%

4-methoxy-N-(pyridin-4-yl)benzamide

Yield 81.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Extractionextracted successively with 1N NaOH, water and brine
2. 2
   Dryingdried over sodium sulfate
3. 3
   Concentrationconcentrated

Procedure

4-Aminopyridine (1.94 g, 20.6 mmol) was added to a solution of p-anisoyl chloride (3.5 g, 20.6 mmol) and triethylamine (8.6 mL, 62 mmol) in dichloromethane (100 mL) at 0° C. The mixture was stirred 3 h at RT, and then extracted successively with 1N NaOH, water and brine, dried over sodium sulfate, and concentrated. Chromatography on silica (gradient of 30% to 100% ethyl acetate-hexanes) gave 3.8 g (81%) of a colorless solid. 1H NMR (CDCl3, 400 mHz) δ 8.49 (m, 2H), 8.19 (br, 1H), 7.85 (m, 2H), 7.59 (m, 2H), 6.95 (m, 2H), 3.85 (s, 3H), MS (AP+) 229 (MH+).

Source