O-Phenylenediamine → HCID 60001261, compound

Participants

Reaction Conditions

Reaction Steps

Benzene-1,2-diamine (2.60 g, 25 mmol) and 2-methyl-5-nitrobenzoic acid (5.0 g, 27.6 mmol) were suspended in polyphosphoric acid (30 ml, 11 vol) and heated to 140° C. overnight. Once the reaction had gone to completion (monitored by LCMS), the crude green mixture was dissolved in water, basified with NaOH (pH=14) and extracted into EtOAc (×2). The organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 7 (4.70 g, 74%) as an orange/brown solid: 1H NMR (C2D6SO) δ 13.20 (s, 1H), 8.80 (app d, 1H), 8.84 (dd, 1H), 7.89-7.87 (m, 2H), 7.74 (d, 1H), 7.40-7.45 (m 2H), 2.90 (s, 3H); MS (ES, positive mode): 254 [M++1].

Provenance & Evidence