Reaction #740889

Reaction equation

methyl 2-amino-5-chlorobenzoate

triethylamine

valeryl chloride

→

crystals

Yield 61.0%

Methyl 5-chloro-2-valerylaminobenzoate

Yield 61.0%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for further two hours
3. 3
   WashThe reaction mixture was washed with an aqueous solution of sodium bicarbonate and water
4. 4
   Otherby drying
5. 5
   workup.DISTILLATIONThe solvent was distilled off

Procedure

To a solution of methyl 2-amino-5-chlorobenzoate (15 g) and triethylamine (12 ml) in methylene chloride (150 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (10 ml). The mixture was stirred at room temperature for further two hours. The reaction mixture was washed with an aqueous solution of sodium bicarbonate and water, followed by drying. The solvent was distilled off to afford a pale yellow crystals (13.4 g, 61%), m.p. 48°-49° C.

Source