Methyl 4-aminobenzoate → HCID 57550196, compound

Participants

Reaction Steps

A mixture of 1-fluoro-2-nitrobenzene (0.46 g, 3.3 mmol) and methyl 4-amino-benzoate (0.5 g, 3.3 mmol) was cooled in an ice-bath, treated dropwise with a solution of potassium tert-butoxide (0.5 g, 4.9 mmol) in DMSO, stirred at room temperature overnight, quenched with water at 0° C. and extracted with ethyl acetate. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound in 56% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 9.5 (s, 1H), 8.22 (d, J=8 Hz, 1H), 8.06 (d, J=8.4 Hz, 2H), 7.46 (d, J=4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 6.91 (m, 1H), 3.92 (s, 3H). LCMS (ESI+) 272 (MH+).

Provenance & Evidence