Sodium Hydroxide → Sodium alpha-(o-aminophenyl)-p-bromocinnamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of FeSO4.7H2O (163 g, 0.586 mol) in 180 ml of water was added 720 ml of 2.5N NaOH and the mixture was stirred and heated at 80° C. A solution of cinnamic acid derivative 1 (20.40 g, 0.05859 mol) in 180 ml of 0.5N NaOH was added dropwise. After the addition was complete, the temperature was increased to 100° C. and maintained for 30 min. The mixture was filtered while hot, and the filtrate was allowed to cool gradually to room temperature. The resulting solid was isolated by filtration to yield, after drying in vacuo, 12.1 g (61%) of the title compound as a tan solid which was used in the next reaction without purification. 1H-NMR (300 MHz, 2:1 D2O/CD3CN): δ 6.95-7.15 (m,3H), 7.18 (d,J=7.3 Hz,2H), 7.39 (t, J=7.6 Hz, 1H), 7.53 (d, J=7.3 Hz,2H), 7.72 (s, CH=C, 1H).

Provenance & Evidence