Formic Acid → HCID 89536255, compound

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (2.63 mL, 27.9 mmol) was added to formic acid (1.04 mL, 27.9 mmol) at 0° C. The mixture was heated to 60° C. for 30 minutes. After that 2-(6-aminobenzo[d]isoxazol-3-yl)isoindoline-1,3-dione 1-4 (390 mg, 1.39 mmol) dissolved in CH2Cl2 (10 mL) was added at 0° C. The mixture was stirred for 1 h at room temperature. The mixture was concentrated and the residue was triturated with CH2Cl2/hexane (1:1) to give 300 mg (70%) of 1-5 as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) (rotamer ratio: s-cis/s-trans=3:1) δ 10.75 (0.75H, br s), 10.58 (0.25H, br d, J=11.3 Hz), 9.04 (0.25H, br d, J=11.3 Hz), 8.43 (0.75H, br s), 8.29 (0.75H, br s), 8.07 (2H, m), 7.99 (2H, m), 7.81 (1H, d, J=8.4 Hz), 7.80 (0.25H, br s), 7.43 (0.75H, d, J=8.4 Hz), 7.28 (0.25H, br d, J=8.4 Hz); ESI-MS m/z 308 [C16H9N3O4+H]+.

Provenance & Evidence