Hydrochloric Acid → HCID 86687922, compound

Participants

Reaction Conditions

Reaction Steps

To crude 2-(bromomethyl)-4-methoxy-5-nitrobenzoate (<4 mmol) in methanol (36 mL) was added Et3N (0.68 mL, 4.8 mmol) and methylamine in EtOH (0.6 mL, ˜8 M in EtOH, 4.8 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 impure 5-methoxy-2-methyl-6-nitroisoindolin-1-one (487 mg) as a brown solid. The crude material was used directly in the next reaction without any further purification.

Provenance & Evidence