2-Amino-5-(benzyloxy)-4-methoxybenzonitrile synthesis

5synthesis methods

Product Name:2-Amino-5-(benzyloxy)-4-methoxybenzonitrile
CAS Number:192869-57-1
Molecular formula:C15H14N2O2
Molecular Weight:254.28

Benzonitrile, 4-Methoxy-2-nitro-5-(phenylMethoxy)-

192869-56-0
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2-Amino-5-(benzyloxy)-4-methoxybenzonitrile

192869-57-1
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Yield:192869-57-1 73%

Reaction Conditions:

with hydrogenchloride;tin(ll) chloride in water;acetic acid at 60; for 1 h;

Steps:

2.4. 2-Amino-5-(benzyloxy)-4-methoxybenzonitrile (5)

Nitro compound 4 (1.00 g, 3.52 mmol) was added to a solution of SnCl₂ (2.00 g, 10.55 mmol) in concentrated hydrochloric acid (4 mL) and acetic acid (14 mL), and the resulting solution was stirred at 60 C. After 1 hour, the solution was allowed to cool down to room temperature. The pH was made basic (pH 10), by addition of 2 M NaOH solution. The solution was extracted with dichloromethane, dried (MgSO₄), and evaporated to give a residue which was purified by column chromatography, eluting by hexane/ethyl acetate (4:1, 1:1) to provide 5 (0.65 g, 2.56 mmol) in 73% yield: ¹H NMR (400 MHz, CDCl₃, δ): 7.42-7.28 (m, 5H), 6.81 (s, 1H), 6.23 (s, 1H), 5.01 (s, 2H), 4.19 (b, 2H), 3.85 (s, 3H); ¹³C NMR (100.6 MHz, CDCl₃, δ): 155.5, 146.6, 140.6, 136.5, 128.6, 128.1, 127.5, 118.1, 117.0, 99.0, 86.3, 72.1, 55.9; IR (KBr): 3359, 2202, 1508 cm^-1; MS m/z: 254.2 (M⁺, 18.5), 163.1 (100.0), 135.1 (21.8), 91.1 (59.3), 77.1 (3.7); HRMS-EI (m/z): [M]⁺ calcd for C₁₅H₁₄N₂O₂, 254.1055; found, 254.1061.

References:

Yin, Kai-Hao;Hsieh, Yi-Han;Sulake, Rohidas S.;Wang, Su-Pei;Chao, Jui-I.;Chen, Chinpiao [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 22,p. 5247 - 5250] Location in patent:supporting information

52805-46-6 Synthesis