Reaction #1106

Reaction equation

4-chloro-3-methoxy-2-methylpyridine

4-tert-butylaniline

NaOH

→

4-(4-tert-Butylanilino)-3-methoxy-2-methylpyridine

Solvents

phenol

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionthe product is extracted
3. 3
   ConcentrationAfter concentrating
4. 4
   workup.DISTILLATIONthe excess of amine is distilled off in vacuo
5. 5
   Otherthe residue is crystallized

Procedure

7.9 g of 4-chloro-3-methoxy-2-methylpyridine and 22.4 g of 4-tert-butylaniline are heated at 120° C. for 8 hours in 20 g of phenol. After cooling, the mixture is poured into NaOH and the product is extracted using methylene chloride. After concentrating, the excess of amine is distilled off in vacuo and the residue is crystallized using hexane. 9.5 g=55%

Source