Ammonium Chloride → 2-Methoxy-4-(2-methylsulfanyl-ethoxy)-phenylamine

Step B A suspension of 2-methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzene (0.25 g, 1.0 mmol) in methanol (8 mL) was added an aqueous solution (4 mL) of NH4Cl (0.55 g, 10 mmol), followed by activated Zinc (Aldrich, 0.67 g, 10 mmol). The reaction mixture was stirred at room temperature for 0.5 h. The mixture was filtered through a short pad of celite. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 2-methoxy-4-(2-methylsulfanyl-ethoxy)-phenylamine as a brown oil (0.2 g, 91%).

1. filtrationThe mixture was filtered through a short pad of celite
2. concentrationThe mixture was concentrated
3. customThe residue was partitioned between ethyl acetate and water
4. customThe organic layer was separated
5. extractionaqueous layer was extracted with ethyl acetate
6. extractionThe combined organic extract
7. washwas washed with water, brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated

ORD record

ord-e9b9243913e3447a9ac20a1886329014

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088815B2