4-Amino-3-chlorobenzonitrile synthesis
- Product Name:4-Amino-3-chlorobenzonitrile
- CAS Number:21803-75-8
- Molecular formula:C7H5ClN2
- Molecular Weight:152.58
873-74-5
21803-75-8
Step 1: N-chlorosuccinimide (12.4 g, 93 mmol) was slowly added to a stirred solution of 4-aminobenzonitrile (10.0 g, 84.7 mmol) in acetonitrile (100 mL) at 90 °C. After the addition was completed, the reaction mixture was stirred continuously at 90 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The concentrated residue was dissolved in 500 mL of dichloromethane and washed with 5% aqueous sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-amino-3-chlorobenzonitrile as a brown solid (12.2 g, 95% yield).1H NMR (300 MHz, CDCl3) δ 7.54 (d, J = 1.7 Hz, 1H), 7.35 (dd, J = 1.8,8.4 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H ), 4.63 (br s, 2H).
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21803-75-8
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Yield: 24.5 g (95%)
Reaction Conditions:
with N-chloro-succinimide in dichloromethane;acetonitrile
Steps:
1 (2-chloro-4-cyanoaniline)
3-chloro-4-cyanoaniline. PREPARATION 2 (2-chloro-4-cyanoaniline) To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux. After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours. The solvent was then removed under reduced pressure. The residue was then dissolved in dichloromethane, washed with a 5% sodium hydroxide solution, dried (Na2 SO4) and evaporated under reduced pressure to afford 24.5 g (95%) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.
References:
Syntex (U.S.A.) Inc. US5034410, 1991, A
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