Phosphorus oxybromide → HCID 85866300, compound

Participants

Reaction Conditions

Reaction Steps

2-(2′-Methylphenylamino)benzoic acid 7 (1.0 g, 4.4 mmol) was suspended in 11.0 g (38 mmol) of phosphorus oxybromide, and the mixture was heated to 120° C. for 2 hours. Excess phosphorus oxybromide was removed by distillation and the residual solution was poured into a 1:1 mixture of aqueous ammonium hydroxide:CH2Cl2. The CH2Cl2 solution was separated, dried, filtered, and the combined organic layers were dried in vacuo to give 9 (1.0 g, 85%) as a yellow powder. 1H-NMR δ=2.94 (s, 3H), 7.53 (dd, J=8.5 Hz, J=8.8 Hz, 1H), 7.59-7.69 (m, 2H), 7.78 (ddd, J=1.4 Hz, J=8.5 Hz, J=8.5 Hz, 1H), 8.28 (dd, J=8.5 Hz, J=8.5 Hz, 2H), 8.43 (dd, J=1.4 Hz, J=8.8 Hz, 1H). 13C-NMR δ=19.48, 126.37, 128.49, 128.76, 129.07, 129.28, 129.72, 130.95, 131.15, 131.88, 135.87, 138.12, 148.43, 148.71. Anal. calcd. for C14H10NBr: C, 61.79; H, 3.70; N, 5.15. Found: C, 61.40; H, 3.72; N, 5.05.

Provenance & Evidence