HCID 22229231, compound → HCID 18693204, compound

Participants

Reaction Steps

2-Amino-4-chloro-3'-methoxybenzophenone (3.75 g, 14.3 mmol) was dissolved in 90 mL of 48% hydrobromic acid and the solution was heated at refluxed for 12 h. The solvent was removed by rotary evaporation and the resulting red solid was distributed between saturated sodium bicarbonate (200 mL) and CH2Cl2 (250 mL). The aqueous layer was washed with CH2Cl2 (2×100 mL) and the combined organic layers were dried with sodium sulfate, filtered through celite and concentrated in vacuo to afford 2.95 g (83% yield) of 2-amino-4-chloro-3'-hydroxybenzophenone (22b) as a yellow solid: mp 137-138° C., Rf 0.15 (75:25, hexanes/ethyl acetate). 1H NMR (500 MHz, CDCl3); δ 6.16 (b, 2), 6.55 (dd, 1, J=2.0, 8.5), 6.72 (d, 1, J=1.9), 6.99 (dd, 1, J=2.5, 8.1), 7.05 (t, J=2.0), 7.12 (d, 1, J=7.8), 7.30 (t, 1, 7.8), 7.38 (d, 1, J=8.6). 13C NMR (101 MHz): δ 115.6, 116.1, 116.2, 118.4, 120.3, 121.6, 126.1, 129.5, 135.9, 142.2, 154.3. HRMS (FAB, m-nitrobenzyl alcohol) calcd for C13H10CINO2 (M+H) 248.0046, found 248.0484.

Provenance & Evidence