Reaction #1483119

Reaction equation

HCl

pyridine

2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride

→

2-(2-Hydroxyphenyl)-1,10-Phenanthroline

Solvents

water

water

Conditions

Workup

1. 1
   TemperatureThe resulting solution was heated on a sand bath
2. 2
   workup.DISTILLATIONthe distillate collected in a Dean-Stark trap
3. 3
   Otherto rise back again to 215-220° C.
4. 4
   workup.WAITheld at this temperature for 3 hours
5. 5
   TemperatureThe solution was then cooled to 100° C.
6. 6
   Otherto precipitate a gummy solid
7. 7
   FiltrationThe orange solid was filtered off
8. 8
   Washwashed well with water
9. 9
   Otherdried

Procedure

Concentrated HCl (17.6 mL) and pyridine (16 mL) were mixed together at room temperature. The resulting solution was heated on a sand bath while passing nitrogen over the surface of the solution and the distillate collected in a Dean-Stark trap. The internal temperature of the reaction was allowed to reach 215-220° C. over a 1 hour period. The solution was allowed to cool to 140° C. and 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride (6 g, 18.59 mMole) then added. With good stirring, the temperature of the resulting solution was allowed to rise back again to 215-220° C. and held at this temperature for 3 hours. The solution was then cooled to 100° C. and treated carefully with water (10 mL), then finally poured into an excess of water (70 mL) to precipitate a gummy solid. With good stirring, the pH of the solution was adjusted to 6-7 with solid Na2CO3. The orange solid was filtered off, washed well with water and dried. Yield of the 2-(2-hydroxyphenyl)-1,10-phenanthroline was 4.6 g.

Source