Potassium Carbonate → HCID 46199380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-Phenyl-5-bromo-2-nitrobenzenamine (0.9 g, 3.2 mmol) and 3-carboxyphenylboronic acid (0.64 g, 3.92 mmol) in Toluene: EtOH: H2O (8:8:1) was added K2CO3 (1.4 g, 9.78 mmol). After stirring reaction for 15 min under argon tetrakis (triphenylphosphine) palladium (0.184 mg, 0.016 mol) was added, resulting mixture was then heated at 100° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and extracted three times with water. The aqueous layer was then acidified with 2M HCl to get 4′-nitro-3′-(phenylamino) biphenyl-3-carboxylic acid (0.8. g), 84% yield. 1H NMR (500 MHz, DMSO): δ 7.23 (m, 2H), 7.44 (m, 4H), 7.61 (t, J=7.7 Hz, 1H), 7.83 (d, J=7.7 Hz, 1H), 8.00 (d, J=7.7 Hz 1H), 8.07 (s, 1H), 8.25 (d, J=9 Hz, 1H), 9.50 (s, 1H), 13.15 (bs, 1H). HRMS (ESI) calculated for C19H14N2NaO4: 357.0846, Found: 357.0816.

Provenance & Evidence