Réaction #7597

Équation de réaction

4-chloro-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline

2-fluoro-5-hydroxy-4-methylaniline

hydrogen chloride

→

4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline

Solvants

2-pentanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 45 minutes
3. 3
   TempératureAfter cooling the solid
4. 4
   Filtrationwas filtered off
5. 5
   Lavagewashed with isopropanol

Mode opératoire

A solution of 4-chloro-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline (130 mg, 0.41 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml) containing 5M hydrogen chloride in isopropanol (2 drops) was heated at reflux for 45 minutes. After cooling the solid was filtered off, washed with isopropanol followed by ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]cinnoline as an hydrochloride salt (159 mg, 88%).

Source