Aniline → HCID 58938487, Verbindung

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.C([NH:15][C:16]1[C:21]([C:22](OCC)=[O:23])=[CH:20][N:19]=[CH:18][N:17]=1)(=O)C>C(Cl)Cl>[NH2:15][C:16]1[C:21]([C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:23])=[CH:20][N:19]=[CH:18][N:17]=1

Komponenten

Versuchsvorschrift

To a solution of aniline (336.0 mg, 3.6 mmol) in 7.5 mL of dry CH2Cl2 was slowly added 2.17 mL of Me3Al (2M solution in hexanes) at RT under N2. After 20 min of stirring compound 22 (301 mg, 1.44 mmol) was added to the reaction mixture as a solution in 2 mL of dry CH2Cl2. The reaction mixture was stirred at RT for 16 h and then quenched with NH4Cl (sat.) followed by extraction into CH2Cl2. The combined organic layers were washed with NaHCO3 (sat.), brine and dried over Na2SO4. The crude material was purified by flash chromatography (CH2Cl2/EtOAc) to yield 75.0 mg of the target compound 23 in 24% yield.