Hydrochloric Acid → HCID 86687918, compound

Participants

Reaction Conditions

Reaction Steps

To methyl 2-(bromomethyl)-5-methoxy-4-nitrobenzoate (212 mg, 0.7 mmol) in methanol (6 mL) was added Et3N (0.12 mL, 0.84 mmol) and methylamine in EtOH (0.11 mL, ˜8 M in EtOH, 0.84 mmol). The mixture was heated to 70° C. for 5 h. and then EtOAc (30 mL) and 2M HCl(aq) (30 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic fractions were passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane then EtOAc-10% MeOH in DCM) gave 6-methoxy-2-methyl-5-nitroisoindolin-1-one (117 mg, 75%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=223 at 3.02 min. 1H NMR (400 MHz, CDCl3): δ 7.86 (s, 1H), 7.53 (s, 1H), 4.40 (s, 2H), 4.02 (s, 3H), 3.24 (s, 3H).

Provenance & Evidence