Methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate → Methyl 3-amino-4-(4-chloro-2-methylbutan-2-ylthio)benzoate
Reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([CH3:20])([S:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-])=O)[CH3:5]>CC(O)=O.[Fe]>[NH2:17][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:7]=1[S:6][C:4]([CH3:20])([CH2:3][CH2:2][Cl:1])[CH3:5])[C:11]([O:13][CH3:14])=[O:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate (3.43 g, 10.8 mmol) in AcOH (100 mL) was added iron (2.413 g, 43.2 mmol). The reaction was heated to 70° C. and stirred at that temperature for 2 hours. The solvent was removed under reduced pressure and the resulting paste was diluted with H2O (250 mL). The solution was treated with K3PO4 until pH=6. The aqueous layer was extracted with EtOAc (3×150 mL). The combined organics were washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL) then dried over Na2SO4 and concentrated in vacuo. The product was isolated as a brown solid and used without further purification.