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Example 191 3-{3-bromo-4-[3-(1-pyrrolidinyl)propoxy]phenyl}-2-methyl 5-(trifluoromethyl)-4(3H)-quinazolinone (1) Manufacture of 4-amino-2-bromophenol The target compound was obtained by reducing <strong>[5847-59-6]2-bromo-4-nitrophenol</strong> with iron in a mixed solution of methanol and ammonium chloride aqueous solution. <strong>[5847-59-6]2-bromo-4-nitrophenol</strong> was manufactured by the method described in the literature (J. Org. Chem., Vol. 62, 1997, p. 4504).
With sodium tetrahydroborate; In tetrahydrofuran; water; at 20℃; for 0.5h;
General procedure: A mixture of 3 mL of 0.015 mol L-1 aromatic nitro compound dissolved in tetrahydrofuran (THF), an aliquot of palladium nanoparticles, 300 muL of 2.0 mol L-1 NaCl solution and an aliquot of water were added into a reaction flask, totalizing 9 mL. Then, 900 muL of 0.5 mol L-1 NaBH4 solution freshly prepared was added to the above solution under continuous stirring. The final ratio H2O:THF was 2.3:1. The mixture was stirred at room temperature for 30 min. After this time, diethyl ether was added and the organic phase was separated and analyzed by gas chromatography (GC/MS) (chromatograph AgilentTechnologies model 7820A coupled to mass spectrometer Agilent Technologies model 5975, operating with acolumn HP5-ms).
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