ChemicalBook CAS DataBase List p-Anisidine

p-Anisidine synthesis

13synthesis methods

Product Name:p-Anisidine
CAS Number:104-94-9
Molecular formula:C7H9NO
Molecular Weight:123.15

p-Anisidine is an important intermediate for synthesis of dye, medicine and perfume. Traditional preparation of p-Anisidine uses iron powder or sodium sulfide as reductant, which produces a large amount of waste and results in serious environment pollution problem. Liquid phase catalytic hydrogenation is not only an environmentally benign technique but also of high yield.
Synthesis of p-Anisidine by Hydrogenation with Raney-RuNiC as Catalyst

104-92-7 Synthesis

104-92-7
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104-94-9
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Yield:104-94-9 99%

Reaction Conditions:

with ammonium hydroxide;copper(l) iodide;N,N-dimethylethylenediamine in dimethyl sulfoxide at 130; for 24 h;Sealed tube;Inert atmosphere;Reagent/catalyst;

Steps:

4.2 General procedure for the synthesis of primary arylamines using CuI/DMEDA in NH₄OH/DMSO (Method A)

General procedure: A 10mL-sealed tube was charged with aryl iodides or bromides (1mmol), CuI (19mg, 0.1mmol), and DMEDA (13mg/16μL, 0.15mmol) in NH₄OH (1.5mL, 27% NH₃ in H₂O) and DMSO (0.5mL). The tube was flushed with Ar gas before being capped. The solution was stirred for the given times at 130°C or 110°C. The resulting suspension was cooled to room temperature and saturated aqueous Na₂SO₄ solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL×3). The organic layer was separated, dried over MgSO₄, filtered and concentrated. The residue was purified by flash column chromatography (hexanes/EtOAc=5/1→1/2 or EtOAc) to give the desired primary arylamines.

References:

Jung, Hee Seon;Yun, Taeil;Cho, Yungyeong;Jeon, Heung Bae [Tetrahedron,2016,vol. 72,# 40,p. 5988 - 5993]