(3-Nitrobenzyl)methylamine

General procedure: The desired nitro-substituted benzaldehyde (1 eq, 13.2 mmol, 2.0 g), methylamine (40percent watersolution, 1.1 eq, 14.5 mmol, 0.95 mL) and molecular sieves (3A, 100 mg) were introduced in a screw cap vialand the mixture was heated at 80°C for 24h. After cooling to RT, the mixture was diluted with chloroform (3mL) and filtered. The solvent was removed by rotary evaporation and the crude obtained was redissolved inmethanol (30 mL) and cooled to 0 °C. NaBH4 (1.1 eq, 14.5 mmol, 550 mg) was added in three portions andthe resultant mixture allowed warming to RT and reacting for 24 h. The mixture was then quenched with aq.NH4OH 5percent (10 mL) and the solvent was concentrated by rotary evaporation. The obtained aqueous layer wasextracted with CH2Cl2 (3 x 10 mL). The combined organic extracts were dried over Na2SO4, filtered and thefiltrate was concentrated by rotary evaporation. The residue was purified by silica gel flash chromatographyor distillation under vacuum to give the title compound.A mixture of 3-nitrobenzaldehyde (1.50 g), methylamine hydrochloride (1.35 g), tetraisopropoxytitanium (5.90 mL) and triethylamine (2.79 mL) in ethanol (15 mL) was stirred at room temperature for 12 hrs. To the reaction mixture was added sodium borohydride (0.57 g) and the mixture was stirred at room temperature for 12 hrs. To the reaction mixture was added 2M aqueous ammonia. The resulting inorganic salt was removed by filtration and washed with dichloromethane. The organic layer was separated and the aqueous layer was extracted. with dichloromethane. The organic layers were combined and washed with 1N hydrochloric acid. The aqueous layer was basified with 2N aqueous sodium hydroxide, extracted with dichloromethane and dried (MGSO4). The solvent was evaporated to give the title compound (1.11 g, yield 67percent). 1H NMR (300 MHz, CDC13) 8 ppm: 2.47 (s, 3 H), 3.86 (s, 2 H), 7.49 (t, J = 7.8 Hz, 1 H), 7.62-7. 71 (m, 1 H), 8.06-8. 15 (m, 1 H), 8.20 (t, J = 1.7 Hz, 1 H).Example 42

Molecular Weight:166.18
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:57.8
Heavy Atom Count:12
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes