Sodium Hydroxide → 5,6-Dimethoxy-2-methyl-2,3-dihydro-1H-isoindole--hydrogen chloride (1/1)

Participants

Reaction Steps

23 g (0.1 mol) of N-(6-chloromethyl-3,4-dimethoxybenzyl)-methylamine hydrochloride was added at a temperature of from 15° to 18° C. to a suspension comprising 50 ml of a 50% sodium hydroxide aqueous solution, 230 ml of benzene and 1 ml of a 90% trioctylmethylammonium chloride aqueous solution over a period of 2 minutes. The mixture was stirred for 3 hours, and then the organic layer of the reaction solution was separated, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 50 ml of 6N hydrochloric acid was added to the residue. The mixture was again evaporated under reduced pressure to dryness. The crystalline residue was washed with ethanol to obtain 12.65 g (yield: 51.2%) of the above identified compound. From the filtrate, 1.8 g (yield: 7.8%) of secondary crystals were obtained. The total amount was 14.4 g (total yield: 63.1%). Melting point: 227° C. (decomposed)

Provenance & Evidence