2-Amino-5-Methyl-Benzonitrile

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl[0055] To a solution of 5-methyl-2-nitrobenzonitrile from Example 2, (25.7 g, 0.158 mol) in 643 mL of acetonitrile was added sodium dithionate (128.5 g, 0.739 mol), followed by addition of 600 mL of deionized water at 0° C. The reaction mixture was stirred for 30 minutes at 25° C. The aqueous layer was extracted with ethyl acetate three times, and the combined organic layers were dried over sodium sulfate and evaporated under vacuum to afford a crude yellow solid, which was dried under high vacuum for 24 hours to give 16.4 g of substantially pure title compound (78.4percent). 1H NMR (CDCl3): δ 2.23 ppm (s, 3H, CH3), 6.65 (d, J=8.4 Hz, aromatic), 7.18 (s, aromatic), 7.14 (d, J=8.4 Hz, aromatic).Combine 2-bromo-4-methyl-phenylamine (8.00 g, 43.0 mmol), CuCN (4.62 g, 51.6 mmol), and NMP [(30.] 0 ml) and stir at reflux. After 75 minutes, cool to ambient temperature, pour the mixture onto ice chips and stir for 1 hour. Remove the resulting precipitate by vacuum filtration. Dissolve the precipitate in NH40H and extract with dichloromethane. Combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using [DICHLOROMETHANE/HEXANES] (75: 25) to give 3.39 g (60percent) of an orange solid: mass spectrum (ion spray): m/z = 133.1 (M+1).

Molecular Weight:132.16
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes