ChemicalBook CAS DataBase List 4-Nitrobenzylamine hydrochloride

4-Nitrobenzylamine hydrochloride synthesis

6synthesis methods

Product Name:4-Nitrobenzylamine hydrochloride
CAS Number:18600-42-5
Molecular formula:C7H9ClN2O2
Molecular Weight:188.61

619-72-7 Synthesis

619-72-7
348 suppliers
$11.00/1g

18600-42-5
142 suppliers
$9.00/250mg

Yield:18600-42-5 90%

Reaction Conditions:

Stage #1:4-nitrobenzonitrile with C₄₆H₁₇₈O₄₁Si₄₂;titanium(IV)isopropoxide in toluene at 60; for 9 h;Inert atmosphere;
Stage #2: with hydrogenchloride;water in toluene at 20;Inert atmosphere;chemoselective reaction;Reagent/catalyst;

Steps:

3 4.2. General procedure for the reduction of nitriles
General procedure: To a nitrogen purged screw-caped vial containing 1a (1.0 g, 5.1 mmol, 1.0 equiv) in 6.0 mL of toluene were added TMDS (900 μL, 5.1 mmol, 1.0 equiv) or PMHS (610 μL, 10.2 mmol, 2.0 equiv) and Ti(Oi-Pr)₄ (1.5 mL, 5.1 mmol, 1.0 equiv) at rt. The mixture was then heated at 60 °C for 24 h (the colorless solution turned into black and the conversion of the substrate can be followed up by TLC and/or ¹H NMR). After cooling to rt, the clear solution was acidified using aqueous 1 M HCl (7.7 mL, 1.5 equiv) and the crude mixture was concentrated under reduced pressure. The resulting solid was filtered, washed with pentane (3*50 mL), and dissolved in ethanol. The filtrate was finally concentrated under reduced pressure affording the amine 2a as a hydrochloride salt.

References:

Laval, Stéphane;Dayoub, Wissam;Pehlivan, Leyla;Métay, Estelle;Favre-Reguillon, Alain;Delbrayelle, Dominique;Mignani, Gérard;Lemaire, Marc [Tetrahedron,2014,vol. 70,# 4,p. 975 - 983] Location in patent:supporting information

FullText