2-[(4-methoxyphenyl)methoxy]isoindole-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-methoxybenzyloxy)isoindoline-1,3-dione (200 mg, 0.706 mmol) in MeOH (5 mL) was added hydrazine monohydrate (35.3 mg, 0.706 mmol). The reaction mixture was stirred at 65° C. for 1 h. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc (5 mL). After stirring for 20 min, the mixture was filtered. The filtrate was concentrated in vacuo to afford the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.30 (m, 2H), 6.90 (m, 2H), 4.63 (m, 2H), 3.81 (s, 3H). The solvent was removed in vacuo the resulting residue was diluted with EtOAc (5 mL) After stirring for 20 min the mixture was filtered The filtrate was concentrated in vacuo

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-methoxybenzyloxy)isoindoline-1,3-dione (200 mg, 0.706 mmol) in MeOH (5 mL) was added hydrazine monohydrate (35.3 mg, 0.706 mmol). The reaction mixture was stirred at 65° C. for 1 h. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc (5 mL). After stirring for 20 min, the mixture was filtered. The filtrate was concentrated in vacuo to afford the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.30 (m, 2H), 6.90 (m, 2H), 4.63 (m, 2H), 3.81 (s, 3H). The solvent was removed in vacuo the resulting residue was diluted with EtOAc (5 mL) After stirring for 20 min the mixture was filtered The filtrate was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-hydroxyphthalimide (11.1 g) and p-methoxybenzyl bromide (13.7 ml) in N,N-dimethylformamide (100 ml) is added triethylamine (6.8 g), and the mixture is stirred at room temperature for 1 hour and at 60° to 70° C. for 1 hour. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract solution is washed with diluted hydrochloric acid and water, dried and concentrated under reduced pressure. The residue is crystallized from methanol to give N-p-methoxybenzyloxyphthalimide (17 g). mp. 139°-141° C. extracted with ethyl acetate The extract solution is washed with diluted hydrochloric acid and water dried concentrated under reduced pressure The residue is crystallized from methanol