O-Phenylenediamine → HCID 57721164, compound

Participants

Reaction Steps

3,5-Dihydroxybenzoic acid (21.4 g, 0.14 mol) and o-phenylenediamine (10 g, 0.093 mol) were refluxed in 4M hydrochloric acid (200 mL) at 135° C. for 24 hours under nitrogen. The mixture was cooled to room temperature and then neutralized to pH 6 with sodium hydroxide and then to pH 8 with sodium bicarbonate. The precipitated tan-colored product was isolated by filtration and recrystallized from methanol/water (1:4) to yield tan-colored needles (6.2 g). 1H NMR (DMSO-d6):δ 6.36 (1H, t), 7.04 (2H, d), 7.19 (2H, m), 7.47 (1H, d), 7.62 (1H, d), 9.56 (O—H,2H, s), 12.71 (N—H, 1H, s).

Provenance & Evidence