Reaction #2328984

Reaction equation

6-Chloronicotinyl chloride

2-hydroxy-4-methoxyaniline

triethylamine

THF

THF

→

title compound

6-Chloro-N-(2-hydroxy-4-methoxyphenyl)nicotinamide

Conditions

Workup

1. 1
   Temperaturewas then heated
2. 2
   Temperatureto reflux for 5 minutes
3. 3
   Otherwas collected
4. 4
   Washrinsed with water
5. 5
   Dryingdried (under vacuum over P2O5)

Procedure

6-Chloronicotinyl chloride (2.0 g, 11.4 mmol) in THF (10 mL) was added dropwise to a mixture of 2-hydroxy-4-methoxyaniline (1.58 g) and triethylamine (1.8 mL) in THF (20 mL) at r.t. The reaction was stirred at r.t for 30 minutes and was then heated to reflux for 5 minutes. After cooling to r.t. the solid was collected, rinsed with water, dried (under vacuum over P2O5), to give the title compound (1.77 g) as an orange solid. 1H NMR δ ppm 9.78 (br. s, 1H) 9.63 (br. s, 1H) 8.94 (d, 1H) 8.34 (dd, 1H) 7.68 (d, 1H) 7.34 (d, 1H) 6.49 (d, 1H) 6.42 (dd, 1H) 3.71 (s, 3H); MS m/z (M+H) 279, 281; (M−H) 277, 279.

Source