HCID 10488759, compound → HCID 21191337, compound

Participants

Reaction Steps

Similar reaction of (E)-3-(acetylamino)cinnamic acid and crude 3-chloromethyl-6-nitroindoline (6) (prepared as in Example 2) gave a crude product which was recrystallised from DMF/MeOH/H2O to give 1-[(E)-3-(acetylamino)cinnamoyl]-3-chloromethyl-6-nitroindoline (13) (80%), mp 229-230° C. 1H NMR [(CD3)2SO] δ10.06 (s, 1 H, NH), 8.97 (s, 1 H, H-7), 7.99 (dd, J=8.3, 2.3 Hz, 1 H, H-5), 7.86 (s, 1 H, H-2), 7.73-7.61 (m, 2 H, H-4,4′), 7.66 (d, J=15.3 Hz, 1 H, PhCH═CH), 7.53 (d, J=7.8 Hz, 1 H, H-6), 7.38 (t, J=7.9 Hz, 1 H, H-5), 7.08 (d, J=15.4 Hz, 1 H, PhCH═CH), 4.65 (t, J 10.0 Hz, 1 H, H-2), 4.33 (dd, J=10.7, 5.2 Hz, 1 H, H-2), 4.14-4.00 (m, 3 H, H-3, CH2Cl ), 2.07 (s, 3 H, CH3).

Provenance & Evidence