Methyl iodide → HCID 13746033, compound

Participants

Reaction Steps

A solution of 3a,4,5,9b-tetrahydro-6,7-dimethoxy-9-methyl-1H-benz[e]isoindole-1,3-(2H)-dione (1.66 g, 6.1 mmole) and dry DMF (28 mL) was stirred under N2 at 0° as a suspension of NaH (60% in oil, washed with hexane, 0.25 g, 6.4 mmole) and DMF (2.8 mL) was added portionwise. The reaction mixture was stirred for 0.5 hour at 0°, and for 0.5 hour at room temperature, then was cooled again at 0° as methyliodide (9.41 mL, 6.6 mmole) was added dropwise. After one hour at 0° and 1.5 hours at room temperature, the reaction mixture was poured onto ice water. The solid was filtered, washed with water, dried (in vacuo) to yield 1.60 g yellow solid (91%), mp 167°-9° C.; M+ 289.

Provenance & Evidence