ChemicalBook CAS DataBase List 2-amino-5-methoxy-4-phenylmethoxybenzamide

2-amino-5-methoxy-4-phenylmethoxybenzamide synthesis

8synthesis methods

Product Name:2-amino-5-methoxy-4-phenylmethoxybenzamide
CAS Number:60547-98-0
Molecular formula:C15H16N2O3
Molecular Weight:272.3

4-(benzyloxy)-5-Methoxy-2-nitrobenzonitrile

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2-amino-5-methoxy-4-phenylmethoxybenzamide

60547-98-0
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Yield: 2.7 g

Reaction Conditions:

with iron;ammonium chloride in water;isopropyl alcohol for 4 h;Reflux;

Steps:

1 2-Amino-4-(benzyloxy)-5-methoxybenzamide (4)
A mixture of compound 3 (5.0 g, 17.6 mmol), iron dust (3.0 g, 54.8 mmol), and ammonium chloride (3.8 g, 70.4 mmol) in isopropyl alcohol-water (2:1) 50 mL was heated to reflux for 4 h. Then, the reaction mixture filtered through celite and the filtrate part was extracted with 5% methanol in DCM. The organic part was dried, concentrated and purified by silica gel chromatography with 10% methanol in DCM to afford compound 4 as light yellow solid (2.7 g, 52% yield). ¹H NMR (300 MHz, CDCl₃) δ 3.89 (s, 3H),5.15 (s, 2H),6.20 (s, 1H),6.88 (s, 1H),7.29-7.51 (m, 5H).FAB [M+H]⁺: 272.6.

References:

COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH;TALUKDAR, Arindam;GANGULY, Dipyaman;PAUL, Barnali;MUKHERJEE, Ayan;ROY, Shounak;ROY, Swarnali;GHOSH, Amrit Raj;BHATTACHARYA, Roopkatha;RAHAMAN, Oindrila;KUNDU, Biswajit WO2017/163264, 2017, A1 Location in patent:Page/Page column 27; 28