Ammonia → 5-nitro-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

AIBN (58.6 mg, 0.357 mmol), NBS (785 mg, 4.46 mmol), and 2-methyl-4-nitrobenzoic acid methyl ester (696 mg, 3.57 mmol) were suspended in CCl4 (35 mL) in a sealed tube. The above mixture was flushed with N2 for 5 min and heated at 80° C. for 22 h. After cooling, the solid was filtered off and the filtrate was concentrated to dryness to obtain a crude light-brown solid. To above solid was added NH3 (7 N in MeOH, 5 mL), and the mixture was stirred at rt for 2 h and concentrated in vacuo to obtain a yellow solid. This crude solid was triturated with EtOAc (15 mL) and was then cooled at −20° C. The mixture was filtered to obtain the title compound as yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ=4.51 (s, 2H), 7.13 (brs, 2H), 7.91 (d, 1H, J=8.4 Hz), 8.25 (dd, 1H, J=2.0 & 8.4 Hz), 8.48 (d, 1H, J=2.0 Hz), 9.04 (brs, 1H). MS (ES+): m/z 179.22 (100) [MH+]. HPLC: tR32 2.14 min (ZQ2000, polar—5 min).

Provenance & Evidence