Reaction #1182193

Reaction equation

2-Amino-5-chloro-benzoic acid methyl ester

Pyridine

3-(chloromethyl)benzoyl chloride

→

5-chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester

Solvents

methylene chloride

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   workup.ADDITIONwas added
4. 4
   Extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
5. 5
   WashThe organic layer was then washed with saturated brine
6. 6
   Dryingwas dried over sodium sulfate
7. 7
   Concentrationwas then concentrated under the reduced pressure
8. 8
   Otherto precipitate crystals
9. 9
   FiltrationThe precipitated crystals were collected by filtration through Kiriyama Rohto
10. 10
    Washwere washed with ether

Procedure

2-Amino-5-chloro-benzoic acid methyl ester (1.5 g) was dissolved in anhydrous methylene chloride (25 ml). Pyridine (1.4 ml) and 3-(chloromethyl)benzoyl chloride (1.4 ml) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was then washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The precipitated crystals were collected by filtration through Kiriyama Rohto and were washed with ether to give 5-chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester as a useful intermediate (2.4 g, yield 90%).

Source