Reacción #52994

Ecuación de reacción

4-Chlorobutyryl chloride

DIEA

4-amino-2-chlorobenzoic acid methyl ester hydrochloride

DIEA

4-chlorobutyryl chloride

→

4-(4-chlorobutyryl)amino-2-chlorobenzoic acid methyl ester

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   workup.STIRRINGthe mixture was stirred for 24 h
3. 3
   Lavadothe solution was washed successively with 1N HCl, std
4. 4
   SecadoNaHCO3, brine, dried
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3:1)

Procedimiento

To a solution of 4-amino-2-chlorobenzoic acid methyl ester hydrochloride (0.52 g) and DIEA (0.27 mL) in CH2Cl2 (20 mL) at 0° C. under N2 was added 4-chlorobutyryl chloride (0.3 mL) and the mixture was stirred for 4 h at that temperature. DMAP (0.23 mmol) was added and the mixture was stirred at room temperature overnight. 4-Chlorobutyryl chloride (0.3 mL) and DIEA (0.09 mL) were added and the mixture was stirred for 24 h. The mixture was diluted with CH2Cl2 (100 mL) and the solution was washed successively with 1N HCl, std. NaHCO3, brine, dried and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3:1) to yield 4-(4-chlorobutyryl)amino-2-chlorobenzoic acid methyl ester (0.64 g). ESMS: m/z 290 (MH+).

Fuente