2-(AMINOMETHYL)-6-METHYLANILINE synthesis

Yield:911845-89-1 31%

Reaction Conditions:

Stage #1: 2-amino-3-methylbenzamidewith lithium aluminium tetrahydride in tetrahydrofuran; for 4.33 h;Heating / reflux;
Stage #2: with sodium hydroxide;water in tetrahydrofuran at 0;

Steps:

a

a) 2-Aminomethyl-6-methyl-phenylamine Under an atmosphere of argon, a solution 2-amino-3-methylbenzamide (1.2 g, 80 mmol) in THF (25 ml) was added to a suspension of LiAlH₄ (1.52 g, 40 mmol) in THF (25 ml) over 20 min. The suspension was heated to reflux (4 h). For workup, the mixture was cooled to 0° C., and 1.5 ml H₂O, 3 ml 4n NaOH, and 3 ml H₂O were added subsequently. The suspension was dried (Na₂SO₄), and evaporated under reduced pressure. The title compound (338 mg, 31%) was isolated from the residue by chromatographic purification (silica gel, CH₂Cl₂/MeOH (2M NH₃) =9:1). MS: m/e=136 [M⁺]. ¹H NMR (CDCl₃): δ 2.20 (3H, s), 3.92 (2H, s), 6.64 (1H, t), 6.92 (1H, d), 6.99 (1H, d).

References:

US2006/229323,2006,A1 Location in patent:Page/Page column 6