Reaction #1135830

Reaction equation

methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate

SnCl2.H2O

→

methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate

Yield 66.9%

Solvents

EtOH

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux overnight
3. 3
   Otherquenched by water
4. 4
   FiltrationThe mixture was filtered
5. 5
   Extractionthe filtrate was extracted with ethyl acetate
6. 6
   OtherThe combined organic layer was dried
7. 7
   Concentrationconcentrated
8. 8
   Otherpurified by biotage column chromatography

Procedure

To a solution of methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate (241 mg, 0.623 mmol) in EtOH was added SnCl2.H2O (490 mg, 2.37 mmol). The reaction was heated to reflux overnight and quenched by water. The mixture was filtered and the filtrate was extracted with ethyl acetate. The combined organic layer was dried, concentrated and purified by biotage column chromatography to afford methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate (149 mg)

Source