3-CHLORO-5-NITROBENZONITRILE

To a stirred solution of 3-Chloro-5-nitrobenzonitrile (30.0 g) was dissolved in a mixture of water (85 mL) and H2SO4 (250 mL) and heated under an N2 atmosphere at 150 C. for 2 h. The mixture was cooled to ambient temperature and poured onto ice (1 L). The resulting solid was collected by vacuum filtration, and the filtrate was extracted with ethyl acetate. The extract and solid were combined, washed with water and brine, then were dried over MgSO4, filtered, and evaporated. The residue was dissolved in 1:1 water/MeOH (200 mL) with heating, treated with decolorizing charcoal and filtered. Water (100 mL) was added and the mixture was allowed to cool and crystallize. The product was obtained as pale yellow crystals. 1H-NMR (d6-DMSO): delta 14.00 (1H, br s), 8.51 (2H, m), 8.29 (1H, m). 13C-NMR (d6-DMSO): delta 164.9, 149.2, 135.2, 135.0, 134.5, 127.7, 122.9.Concentrated H2SO4 (440 mL) was added slowly to crushed ice (1200 g) and 2-amino-3-Chloro-5-nitrobenzonitrile was reduced to 3-amino-5-chlorobenzonitrile by treating with 6 equivalents of SnCl2 dihydrate in DMF at RT overnight. The product was purified by chromatography over silica gel (40% yield). LCMS (Cond. A) RT 1.61 min., MH+ 153. 1H NMR (500 MHz, CDCl3) delta 6.97 (s, 1H), 6.84 (t, J=2.0 Hz, 1H), 6.77 (s, 1H).

Molecular Weight:182.56
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Exact Mass:181.9883050
Monoisotopic Mass:181.9883050
Topological Polar Surface Area:69.6
Heavy Atom Count:12
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes