(Quinolin-3-yl)methanol → (1,2,3,4-Tetrahydroquinolin-3-yl)methanol

Participants

Reaction Steps

3-Hydroxymethylquinoline (0.45 g, 2.83 mmoles) (prepared as described in: B. R. Brown, D. Ll. Hammick and B. H. Thewlis, J. Chem. Soc., 1951,1145-1149.) was dissolved in methanol (100 mL) and placed in a Parr bomb. Platinum (IV) oxide monohydrate (0.225 g, 0.918 mmoles) was added and the mixture was hydrogenated at 50 psi at 25° C. for 6 h. The catalyst was removed by decantation and washed with methanol. The methanol was evaporated to dryness and the product was chromatographed on silica gel using 3% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (0.3843 g, 83%): CIMS: m/z 164.35 (MH+); δH (CDCl3) 6.50 (1H, d, Ar—H8), 6.64 (1H, t, Ar—H6), 6.98 (1H, d, Ar—H5) and 6.99 ppm(1H, m, Ar—H7); δC (CDCl3) CH2: 29.5, 44.0, 65.2; CH: 34.9, 114.2, 117.4, 126.9, 129.8; C: 120.2, 144.5.

Provenance & Evidence