bis(3-Methoxyphenyl)aMine

λ/-[2-(bis-3-methoxyphenylamino)ethyllacetamide (5c):Cupric acetate (2.1 mmol) and pyridine (0.25 ml) were added to a vigorously stirred solution of 3-methoxyaniline (1 mmol) and 3-methoxyphenylboronic acid (2 mmol) in dry methylene chloride (3.5 ml), under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 72 h (the progress of the reaction was monitored by TLC). λ/-(3-Methoxyphenyl)-3-methoxyaniline (3c) was isolated by direct flash chromatography of the crude reaction mixture following preabsorption on silica gel. Yield (3c): 25percent; EI-MS 229 (MThe advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdClGeneral procedure: In a threaded ACE glass pressure tube with a sealed Teflonscrew cap, under N2 atmosphere, a mixture of 4a (0.20 g, 1.0 mmol) and Pd/C (10percent) (0.060 g, 0.057 mmol) in dry MeOH (2.5 mL) was stirred at 210 °C for 24 h. After removing the solvent undervacuum, K2CO3, (0.200 g, 1.45 mmol) and CH3I (0.281 g, 1.98 mmol) in dry acetone (20 mL) wereadded, and the mixture was heated to reflux for 12 h. The solvent was removed under vacuum and theresidue purified by column chromatography over silica gel (20 g/g of crude, hexane/EtOAc, 90:10), togive 5a (0.176 g, 83percent) as a white solid.The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl

Molecular Weight:229.27
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:229.110278721
Monoisotopic Mass:229.110278721
Topological Polar Surface Area:30.5
Heavy Atom Count:17
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes