Ethanolamine → HCID 20200468, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3.0 g (10 mmol) of methyl ester of N-(2-methoxyphenylacetyl)anthranilic acid and 1.2g (20 mmol) of monoethanolamine in xylene was heated at 180° C. for 16 hours in a sealed tube. After cooling, the precipitated crystals were collected by filtration to obtain 0.7 g (22%) of 2-(2-methoxyphenylmethyl)-3-(2-hydroxyethyl)- 4(3H)-quinazolinone (m.p.: 154°-155° C.). Subsequently, to 0.7 g (2.2 mmol) of this 3-(2-hydroxyethyl) derivative was added thionyl chloride (5 ml) and the resulting reaction mixture was stirred at room temperature for 1 hour. An excess of the thionyl chloride was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:dichloromethane) to obtain 0.14 g (20%) of 2-(2-methoxyphenylmethyl)-3-(2-chloroethyl)-4(3H)-quinazolinone. (m.p.: 109°-111° C.).

Provenance & Evidence