4-Nitrophthalic acid anhydride → HCID 86660587, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4 (0.4 g, 1.08 mmol), 4-nitrophthalic anhydride (0.259 g, 1.34 mmol), and sodium acetate (0.125 g, 1.45 mmol) was added acetic acid (4 mL) and the resulting mixture was stirred at 130° C. After 6 h, the mixture was quenched with sodium bicarbonate and extracted with DCM. The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography (95:5 DCM:MeOH) afforded 9 (0.45 g, 87%). Rf=0.36 (95:5 DCM:MeOH). 1H NMR (400 MHz, CDCl3) δ 8.62 (par obsc s, 1H), 8.60-8.51 (par obsc m, 1H), 8.16-7.86 (m, 2H), 7.44-7.27 (m, 5H), 5.07 (m, 2H), 3.23 (m, 3H), 2.93-2.49 (m, 3H), 2.46-2.23 (m, 1H), 2.14 (m, 1H), 1.79-1.47 (m, 3H), 1.45-1.17 (m, 2H), 1.00-0.75 (m, 1H). MS (ESI) m/z calcd for C25H25N4O8 [M+H]+ 509.5, found 509.3.

Provenance & Evidence