Reaction #1135834

Reaction equation

methyl 8-chloro-8-oxooctanoate

4-nitrobiphenyl-3-amine

triethylamine

→

methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate

Yield 74.8%

Solvents

DMF

DMF

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with 1 N HCl, saturated sodium bicarbonate solution and brine
2. 2
   ConcentrationThe separated organic layer was concentrated
3. 3
   Otherpurified by biotage column chromatography

Procedure

To a solution of methyl 8-chloro-8-oxooctanoate (200 mg, 0.97 mmol) in DMF at 0° C. was added a solution of 4-nitrobiphenyl-3-amine (207 mg, 0.97 mmol) and triethylamine (0.46 mL, 3.3 mmol) in DMF drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated and purified by biotage column chromatography to give methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate (279 mg)

Source