p-Toluidine → Methyl 3-(4-methylanilino)benzoate

Participants

Reaction Steps

Reaction of methyl 3-bromobenzoate with p-toluidine according to general procedure A provided methyl ester of Compound 12 as a yellow oil (69% yield). 1H NMR (CDCl3, 500 MHz): δ=7.68 (s, 1H), 7.55 (d, J=7.6 Hz, 1H), 7.29 (t, J=7.7 Hz, 1H), 7.19 (m, 1H), 7.13 (d, J=8.0 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 5.77 (s, 1H), 3.91 (s, 3H), 2.34 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.4, 144.6, 139.8, 131.9, 131.5, 130.2, 129.5, 121.3, 120.8, 119.7, 117.5, 52.2, 20.9.

Provenance & Evidence