Acetone → HCID 43165626, compound

Participants

Reaction Steps

Zinc dust (3.86 g, 59.1 mmol) was added to a stirred solution of 4-(2,6-dimethyl-phenoxy)-3-methyl-nitrobenzene (1.5 g, 5.9 mmol), acetone (20 mL) and saturated aqueous ammonium chloride (20 mL) at 0° C. The mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with 200 mL EtOAc and filtered through diatomaceous earth. The organic layer was washed with brine, dried with sodium sulfate and concentrated to provide the crude titled compound (0.79 g, 59%). This material was used without purification: MS (ESI): mass calcd. for C15H17NO, 227.3; m/z found, 227.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.07 (d, J=7.2 Hz, 2H), 7.01 (dd, J=8.3, 6.5 Hz, 1H), 6.60 (t, J=3.4 Hz, 1H), 6.31 (dd, J=8.5, 2.9 Hz, 1H), 6.06 (d, J=8.5 Hz, 1H), 3.36 (s, 2H), 2.34 (s, 3H), 2.11 (s, 6H).

Provenance & Evidence