Toluene → 3-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine

Participants

Reaction Steps

A 100 mL round-bottom flask equipped with a N2 inlet was charged with 1-3 (2.54 g, 13.1 mmol), toluene (65 mL), and freshly grounded NaNH2 (2.69 g, 65.5 mmol). The flask was evacuated and back filled with N2 and placed in a 90° C. oil bath. After 15 h, water (1.18 mL, 65.5 mmol) was added slowly without removing the flask from the oil bath. Caution: an exothermic reaction occurs upon addition of water. After the addition of water, the resulting mixture was filtered while hot, followed by 65 mL of hot toluene (90° C.). The mother liquor was concentrated to yield 2.37 g (94%) of 1-4.

Provenance & Evidence