(2-methoxy-5-methylphenyl)methanamine synthesis

Yield:7383-12-2 10%

Reaction Conditions:

in tetrahydrofuran at 0; for 1.25 h;Inert atmosphere;Reflux;

Steps:

71 (2-methoxy-5-methylphenyl)methanamine

(2-methoxy-5-methylphenyl)methanamine
Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-methoxy-5-methylbenzonitrile (1 g, 6.79 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) with stirring at 0° C., to which was added 2M BH₃-Me₂S in tetrahydrofuran solution (12 mL, 4.00 equiv) dropwise with stirring at 0° C. in 10 min. The resulting mixture was stirred for 5 min at 0° C. and refluxed for 1 h. The reaction was then quenched by the addition of 7 mL of methanol. The reaction mixture was concentrated under vacuum. The crude product was purified by Combi-Flash with the following conditions. Column: C 18, 20-45 um, 100 A, 120 g; mobile phase: water (it contains 0.05% ammonia and 10 mM NH₄HCO₃) and acetonitrile with a gradient of 30% to 65% acetonitrile in 12 min; flow rate: 60 mL/min; detector UV wavelength: 254 nm and 220 nm. This resulted in 100 mg (10%) of (2-methoxy-5-methylphenyl)methanamine as white solid. MS (ESI) m/z found for C9H13NO: 152 [M+H]⁺.

References:

US2015/315198,2015,A1 Location in patent:Paragraph 0386