Water → 3-(3,5-Dichloropyrid-2-yloxy)-4-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 14.0 g (0.1 mol) of 5-amino-2-methoxyphenol and 6.7 g (0.1 mol) of potassium hydroxide (85%) in 100 ml of toluene and 100 ml of dimethyl sulfoxide is dewatered at 150° C. in a sulfonating flask equipped with a water separator. After 3 hours the toluene is distilled off, the mixture is cooled to 80° C. and 18.2 g (0.1 mol) of 2,3,5-trichloropyridine in 25 ml of dimethyl sulfoxide are added. The mixture is stirred for 3 hours at 120° C. and then cooled and 5 ml of acetic acid are added. After distillation under a high vacuum, the residue is extracted with 200 ml of water and 300 ml of methylene chloride. The organic phase affords 28 g of 3-(3,5-dichloropyrid-2-yloxy)-4-methoxyaniline as congealing oil. Melting point 95°-105° C.

Provenance & Evidence