Ammonium Chloride → Tert-butyl 4-amino-3-methoxyphenylacetate
Reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:17][CH3:18])[CH:9]=1)([CH3:3])([CH3:4])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Step C A suspension of (3-methoxy-4-nitro-phenyl)-acetic acid tert-butyl ester (3 g, 11.2 mmol) in methanol (100 mL) was added an aqueous solution (50 mL) of NH4Cl (6 g, 112 mmol), followed by activated zinc (Aldrich, 7.3 g, 112 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 (4-amino-3-methoxy-phenyl)-acetic acid tert-butyl ester as a brown oil (2.5 g, 94%).