Nitric Acid → HCID 118286578, compound

Participants

Reaction Steps

Dimethyl 2,2′-((2-methoxyphenyl) azanediyl)diacetate (1.98 g, 7.41 mmol) was dissolved in acetic acid (10 mL) at room temperature followed by sodium nitrite (51 mg, 0.74 mmol). The nitric acid (0.49 mL, 8.15 mmol) was added dropwise to reaction mixture. After stirring 1 h, the reaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 ml×3), and dried over MgSO4. The residue was purified by column chromatography using Hex/EtOAc (gradient: 0 to 50% EtOAc) to afford dimethyl 2,2′-((2-methoxy-4-nitrophenyl)azanediyl)diacetate (1.98 g, 86%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.80 (dd, J=8.8, 2.4 Hz, 1H), 7.69 (d, J=2.4 Hz, 1H), 6.66 (d, J=8.8 Hz, 1H), 4.20 (s, 4H), 3.85 (s, 3H), 3.78 (s, 6H); LCMS (ESI) tR: 0.678 min (>99%, ELSD), m/z: 313.2 [M+1]+

Provenance & Evidence