Acetic Acid → HCID 19858390, compound

Participants

Reaction Steps

A mixture of 4-nitrophthalic anhydride (3.46 g, 17.9 mmol) and 4-aminobenzocyclobutene (2.20g, 18.5 mmol) was refluxed in acetic acid under N2 for about 17 hours. The dark reaction mixture was then allowed to cool to room temperature and poured into 500 ml of H2O, followed by extraction with CH2Cl2 (75 ml+3×50 ml). The dark extract was then washed with approximately 300 ml of H2O and then dried over MgSO4. Complete removal of CH2Cl2 from the extract by rotary evaporator afforded a dark oil, which was purified by column chromatography (150 g silica gel; using 1:1 petroleum ether/CH2Cl2 as eluent). Pure product was isolated from the first fraction as yellow solid. Yield: 3.21 g (65%). Calc. for C16H10N2O4 : 65.30% C; 3.42% H; 9.52% N. Found: 65.21% C; 3.39% H; 9.58% N. Mass spectroscopy: 294 (M+, 100%). Proton NMR (CDCl3): 3.24 (singlet, alicyclic protons). 7.00-7.23, 8.06-8.72 (complex, aromatic protons). IR(KBr): 2900 w, 2770 m, 2650 m (alicyclic C--H stretches); 1720, 1775 (Symmetric and asymmetric stretches of imide group): 1350, 1540 (symmetric and asymmetric stretches of nitro group).

Provenance & Evidence