Application of 21803-75-8,Some common heterocyclic compound, 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, molecular formula is C7H5ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a stirred solution of 4-amino-3-chloro-benzonitrile (8.0 g, 52.4 mmol) and 3-bromobenzaldehyde (6.2 mL, 52.4 mmol) in acetonitrile (150 mL) were added isobutene (14.7 mL, 209.7 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (4.0 g, 6.3 mmol). The resulting mixture was stirred at 85 C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-8-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (7.8 g, 40.0%) as a light yellow solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 374.9 & 376.9.
The synthetic route of 21803-75-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Zhou, Mingwei; US2012/101127; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts