Reaction #363024

Reaction equation

N-methyl-N-methyloxy-2-amino-5-chlorobenzamide

2-(3-bromophenyl)-1,3-dioxolane

hexane

n-butyl lithium

→

3-(2-amino-5-chlorobenzoyl)phenyl-1,3-dioxolane

Yield 57.5%

Solvents

tetrahydrofuran

acetic acid ethyl ester

water

Conditions

Workup

1. 1
   WashThe organic layer was washed with water
2. 2
   Dryingdried over anhydrous Na2SO4
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   OtherThe residue was purified by means of a silica gel column chromatography

Procedure

A solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (2 g) and 2-(3-bromophenyl)-1,3-dioxolane (2.1 g) in tetrahydrofuran (65 ml) was cooled to −78° C. To the solution was added dropwise gradually a hexane solution of n-butyl lithium (1.6 mol/L)(11.6 ml). To the mixture were added water (300 ml) and acetic acid ethyl ester (50 ml). The organic layer was washed with water and dried over anhydrous Na2SO4, then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography to give 2-[3-(2-amino-5-chlorobenzoyl)phenyl-1,3-dioxolane (1.6 g) as a colorless oily compound.

Source