2-Methylbenzylamine → HCID 483318, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), in anhydrous THF (5 ml) at 0° C. was added triethylamine (44 ml, 0.316 mmol). After 5 min, isopropylchloroformate (0.316 ml, 1M solution in toluene, 0.316 mmol) was added. The mixture was stirred at 0° C. for 20 min. then 2-methylbenzylamine (53.46 ml, 0.43 mmol) was added to the mixture at 0° C. The resulting mixture was allowed to warm to room temperature and stirred at room temperature for 5 h then diluted in CH2Cl2 (100 ml). The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (29.8 mg, 37%): m.p. 120-121° C.

Provenance & Evidence