Ammonium Chloride → 3-Amino-2-methylbenzonitrile

To a mixture of 2-methyl-3-nitrobenzonitrile (5.50 g, 33.9 mmol) and ammonium chloride (25.4 g, 475 mmol) in tetrahydrofuran (100 mL) and methanol (100 mL) at 0° C. was added zinc dust (31.1 g, 475 mmol) in portions. The mixture was stirred at room temperature for 2 hr. The insoluble material was removed by suction filtration through CELITE®, and the filtrate was concentrated under vacuum. The residue was diluted with water (50 mL) and extracted with CH2Cl2 (4×100 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (4.19 g, 31.7 mmol, 93% yield) as a white solid.

1. customThe insoluble material was removed by suction filtration through CELITE®
2. concentrationthe filtrate was concentrated under vacuum
3. additionThe residue was diluted with water (50 mL)
4. extractionextracted with CH2Cl2 (4×100 mL)
5. extractionThe combined extract
6. dry with materialwas dried over anhydrous MgSO4
7. customRemoval of solvent under vacuum

ORD record

ord-d92ae08ba65d46718990ad7be9884318

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2