Sodium hydride → 2-Methyl-8-hydroxyquinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-fluorobenzyl alcohol (1.95 g, 15.5 mmol) in anhydrous DMF (35 mL) was added sodium hydride (60% in mineral oil, 0.62 g, 15.5 mmol). After 30 min the 4-chloro-2-methylquinolin-8-ol (1.00 g, 5.16 mmol) was added and resulting mixture was heated at 130° C. for 20 h under nitrogen atmosphere. The mixture was cooled, poured into ice/NaHCO3 and extracted with EtOAc. Evaporation gave a crude oil that was purified by silica chromatography eluting with a gradient of 1% to 10% of MeOH/DCM to give 44(2-fluorobenzyl)oxy)-2-methylquinolin-8-ol as an oil that solidified on standing (0.39 g, 27%). LCMS (+APCI) 284 (M+1), mp 124-125° C. 1H-NMR (CDCl3, δ): 7.75 (d, J=8.4 Hz, 1H), 7.50 (d, J=7.6 Hz, 2H), 7.43 (s, 1H), 7.35 (m, 3H), 7.20 (d, J=7.6 Hz, 1H), 7.06 (d, J=8.0 Hz), 5.45 (s, 2H), 2.78 (s, 3H).

Provenance & Evidence