Aluminium lithium hydride → HCID 24957319, compound

Participants

Reaction Steps

A solution of LiAlH4 (1 M in ether, 1.98 mL, 1.98 mmol) is added dropwise to a solution of 3-(3,3-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid ethyl ester (621 mg, 1.98 mmol) in THF (10 mL) at −10° C. After 4 h at this temperature, the reaction is quenched by the addition of water (0.3 mL), NaOH solution (15%, 0.3 mL) and water (1 mL). The resulting mixture is filtered, and the solid is washed by ether (10 mL×3). The combined solution is concentrated under vacuum, and the residue is purified by reverse phase HPLC (5% to 40% acetonitrile/water with 0.1% NH4OH over 15 min) to give the title compound (445 mg). 1H NMR (400.3 MHz, MeOD): δ 7.43 (d, J=8.0 Hz, 1H) 7.39 (s, 1H), 7.35 (t, J=8 Hz 1H), 7.09-7.03 (m, 2H), 6.91 (s, 1H), 5.39 (s, 1H), 4.72 (d, J=8.0 Hz, 2H) 1.30 (s, 3H), 1.05 (s, 3H), 13C NMR (100.6 MHz, MeOD): δ 175.93, 138.02, 136.50, 133.43, 131.20, 130.68, 127.52, 124.80, 123.29, 117.07, 61.88, 54.40, 25.68, 19.97. HRMS: calculated for C15H17N3O2: 272.1399. Found: 272.1407.

Provenance & Evidence