Methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate → Methyl 3-amino-4-(4-chloro-2-methylbutan-2-ylthio)benzoate

Temperature

70 °C

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.

1. customThe solvent was removed under reduced pressure
2. additionthe resulting paste was diluted with H2O (250 mL)
3. additionThe solution was treated with K3PO4 until pH=6
4. extractionThe aqueous layer was extracted with EtOAc (3×150 mL)
5. washThe combined organics were washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
6. dry with materialthen dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe product was isolated as a brown solid
9. customused without further purification

ORD record

ord-217da6b6e262468e83e12698184952bb

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960376B2