N,2-Dimethylbenzenemethanamine

To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25° C. was added methylamine (40 percent in HTo a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25 C. was added methylamine (40 % in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25 C. for 30 min after which time it was cooled to 0 C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25 C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired Step A: o-Tolualdehyde was converted to General procedure: 5-Chloro-2, 3, 4-trimethoxybenzaldehyde (1.01 g, 4.35 mmol) and 40% methylamine (0.20 g, 6.54 mmol) in methanol was stirred at room temperature for 30 min. Sodium borohydride (0.08 g, 2.18 mmol) was added at 0 C and was stirred for 1 h. The mixture was added water, methanol removed under reduced pressure and then extracted with dichloromethane three times. The organic layer was dried over Na2SO4, concentrated under reduced pressure to afford compound 9f in 89% yield.17. 5-chloro-2, 4-dihydroxy-N-methyl-N-(2-methylbenzyl)benzamide (16a) Compound 15 (0.17 g, 0.92 mmol), Compound 8a (0.19 g, 1.40 mmol), HOBt (0.12 g, 0.92 mmol), EDC (0.35 g, 1.86 mmol) and DIPEA (0.16 mL, 0.92 mmol) were dissolved in DMF and microwave reaction was performed at 120 C. and 20 bar for 3 hours. It was dissolved in EA, washed with a saturated aqueous solution of 1N HCl, dried over Na2SO4 and filtered. The solvent was removed by distillation under reduced pressure to obtain Compound 16a in a. The residue was purified by MPLC (Rf=0.23, EA:hexane=1:4) to obtain Compound 16a in a yield of 90.5%. 1H NMR (400 MHz, CDCl3) d 7.25-7.24 (m, 4H), 6.65 (s, 1H), 4.72 (s, 2H), 3.07 (s, 3H), 2.27 (s, 3H). 13C NMR (100 MHz, CDCl3) d 160.9, 155.2, 136.4, 134.0, 131.0, 128.7, 128.0, 127.4, 126.7, 110.7, 110.2, 105.3, 19.2.

Molecular Weight:135.21
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:135.104799419
Monoisotopic Mass:135.104799419
Topological Polar Surface Area:12
Heavy Atom Count:10
Complexity:90.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes