Ammonium Hydroxide → 4-Amino-3-methylbenzonitrile

4-Cyano-2-methylaniline was synthesized as previously described (J. Med. Chem. (1991), 34, 3295): To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.34 mmol) in acetic acid (20 L) was added dropwise a solution of SnCl2 (9.6 g, 49.38 mmol) in conc. HCl (20 mL). After stirring for 3 h, the mixture was added carefully to a saturated NH4OH solution (120 mL) at 0° C. The resulting mixture was extracted with EtOAc (4×30 mL). The combined organic layers were sequentially washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (10% EtOAc/hex) to give 4-cyano-2-methylaniline as a white solid (1.48 g, 92%): TLC (30% EtOAc in hexane) Rf0.23. This material was used without further purification.

1. custom4-Cyano-2-methylaniline was synthesized
2. extractionThe resulting mixture was extracted with EtOAc (4×30 mL)
3. washThe combined organic layers were sequentially washed with H2O (30 mL)
4. dry with materiala saturated NaCl solution (30 mL), dried (Na2SO4)
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by flash chromatography (10% EtOAc/hex)

ORD-Eintrag

ord-44cc49bea78a4a69bac44e5def73b036

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06353006B1