HCID 25140617, compound → HCID 25139618, compound

Participants

Reaction Steps

A suspension of nitroacetamide 92 (3.79 g, 16.2 mmol) in EtOH (100 mL) and cHCl (14 mL) was stirred at reflux temperature for 4 h. The mixture was cooled and the EtOH evaporated. The mixture was diluted with water (100 mL) and the pH adjusted to 9 with cNH3. The mixture was extracted with DCM (3×50 mL) and the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with 20% EtOAc/pet. ether, to give nitroaniline 93 (3.01 g, 97%) as a red solid: mp (EtOAc/pet. ether) 100-101° C.; 1H NMR δ 7.89 (s, 1H, H-7), 6.61 (s, 1H, H-4), 5.99 (br s, 2H, NH2), 2.92-2.99 (m, 2H, CH2), 2.40-2.58 (m, 3H, H-2, CH2), 1.12 (d, J=6.5 Hz, 3H, CH3); 13C NMR δ 153.9, 144.3, 133.6, 131.3, 120.9, 113.6, 41.1, 39.6, 34.8, 20.4. Anal. calcd for C10H12N2O2: C, 62.5; H, 6.3; N, 14.6. Found: C, 62.6; H, 6.3; N, 14.5%.

Provenance & Evidence