HCID 22667729, compound → HCID 22667746, compound

Participants

Reaction Steps

To a solution of [(5-bromo-2-nitro-phenyl)-isopropyl-amino]acetic acid (27 g, 85 mmol) in acetic acid (400 ml) was added iron powder (15 g, 0.27 mol) and the mixture was stirred for 2 hrs. at 90° C. The reaction mixture was cooled, filtered, and the acetic acid was evaporated. The remaining slurry was extracted with CH2Cl2 (3×300 ml). The CH2Cl2 extracts were combined, dried (MgSO4) and evaporated to afford the subtitled compound (16.8 g, 73%): 1H-NMR (DMSO-d6) δ 1.13 (d, J=6.54 Hz, 6H), 3.57 (s, 2H), 3.99 (septet, J=6.54 Hz, 1H), 6.82 (dd, J=8.23, 1.88 Hz, 1H), 6.72 (d, J=8.17 Hz, 1H), 6.90 (d, J=1.59 Hz, 1H), 10.50 (s, 1H): MS (EI) 267/269 (M)++1 bromine.

Provenance & Evidence