Reaction #1135835

Reaction equation

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

ammonium formate

→

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

Yield 85.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux under a nitrogen atmosphere overnight
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated
5. 5
   Otherpurified by biotage column chromatography

Procedure

To a solution of methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate (270 mg, 0.70 mmol) and ammonium formate (177 mg, 2.8 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give methyl 8-(4-aminobiphenyl-3-ylamino)-8-oxooctanoate (211 mg)

Source