Aluminium lithium hydride → HCID 178519383, compound

Participants

Reaction Steps

Under a nitrogen atmosphere a dry round-bottom flask was charged with LiAlH4 (0.316 g, 7.90 mmol) and THF (15 mL). Methyl 1H-benzo[d][1,2,3]triazole-5-carboxylate (1.0 g, 5.64 mmol) was then added portion-wise over 10 min at room temperature and reaction allowed to stir for 4 hours at which time the reaction was quenched with EtOAc (5 mL), and the mixture poured into ice-water. The mixture was acidified to pH=3 with 10% H2SO4 and extracted 4× with EtOAc. The combined organics were washed with brine, dried (MgSO4) and the solvent removed. The resulting brown solid was boiled in Et2O and the solids filtered and dried to give the title compound as a light brown solid (678 mg, 81%). 1H NMR (400 MHz, CD3OD) δ 7.85 (m, 2H), 7.47 (d, J=8.4 Hz, 1H), 4.79 (s, 2H); MS ESI 150.0 [M+H]+, calcd for [C7H7N3O+H]+150.16.

Provenance & Evidence