Sodium hydride → 3-(Aminomethyl)benzoic acid hydrochloride

関与物質

反応条件

反応手順

4.34 g (20.0 mmol) of di(t-butyl) iminodicarboxylate was added to a mixture of 800 mg (20.0 mmol) of sodium hydride (60% dispersion in mineral oil) and 50 ml of dimethylformamide. 1.71 g (10.0 mmol) of 3-chloromethylbenzoic acid was added to the obtained mixture, and they were stirred at 80° C. for 2 hours. After the concentration under reduced pressure, 40 ml of dioxane containing 4 M of hydrogen chloride was added to the residue, and they were stirred at room temperature overnight. A white precipitate thus formed was taken by the filtration and washed with ethyl acetate to obtain 3-aminomethylbenzoic acid hydrochloride as white crystals. A mixture of this aminomethyl compound, 10 ml of water, 10 ml of 28% aqueous ammonia and 3.00 g (71.4 mmol) of cyanamide was stirred at 60° C. for 7 days. The solvent was evaporated, and the residue was purified by the reversed-phase HPLC in the same manner as that in step 5 in Example 1 to obtain the title compound.

情報源と証拠