2-(Dimethylamino)ethanol → HCID 58967008, compound

Participants

Reaction Steps

A flame-dried round-bottomed flask was charged with 4,5-difluoro-2-nitroaniline (2.00 g, 11.49 mmol) and N,N-dimethylethanolamine. Pyridine (44 mL) was added followed by slow addition of NaH (60% in mineral oil, 965 mg, 24.1 mmol). The mixture was put under N2 atmosphere, stirred at rt for 16 h and quenched with H2O. Solvents were removed in vacuo and the residue was partitioned between H2O and EtOAc. The organic layer was extracted twice with HCl 1N, the combined acidic extracts were neutralized with saturated NaHCO3 to form a precipitate which was allowed to stand overnight, collected by filtration and purified by flash chromatography using MeOH/CHCl3 with increasing polarity (10:90 to 15:85) to afford the title compound 180 (1.30 g, 47% yield). 1H NMR: (CD3OD) δ (ppm): 7.76 (d, J=11.7 Hz, 1H), 6.53 (d, J=7.4 Hz, 1H), 4.19 (t, J=5.5 Hz, 2H), 2.84 (t, J=5.5 Hz, 2H), 2.37 (s, 6H). m/z: 244.2 (MH+).

Provenance & Evidence