Acetanilide → HCID 762824, compound

Participants

Reaction Steps

The title compound was prepared following Method A at larger scale, from 4-chloro-3-nitrobenzoic acid methyl ester (5.39 g, 25 mmol), N-phenylacetamide (3.38 g, 25 mmol), palladium trifluoroacetate (416 mg, 1.25 mmol), BINAP (778 mg, 1.25 mmol) and Cs2CO3 11.4 g, 35 mmol) and refluxing just for 5 hours, giving rise to the title compound as colorless crystals (5.19 g, 78%). mp 108° C. to 110° C. 1H NMR (DMSO) δ 2.55 (s, 3H), 3.78 (s, 3H), 7.30 (d, J=8.2Hz, 1H), 7.52-7.71 (m, 5H), 7.92 (d, J=8.2Hz, 1H), 8.30 (br s, 1H); 13C NMR δ 13.6, 52.1, 110.8, 118.5, 124.7, 124.8, 127.0, 129.7, 130.1, 134.0, 137.9, 153.7, 157.8, 166.2. HRMS (FAB): cal. for C16H15N2O2 [M+H+]: 267.1134; found: 267.1128.

Provenance & Evidence