Sodium Hydroxide → 9'-methoxy-1,3,3-trimethylspiro [benz[g] indoline-2,3'-[3H] naphth [2,1-b][1,4] oxazine]

Participants

Reaction Steps

To a solution of 1.05 grams (3.0 mmole) of 1,2,3,3-tetramethyl-3H-benz[g] indolium iodide in 15 milliliters (ml) of hexane at 25° C. was added 10 ml (50 mmole) of 20% sodium hydroxide. The two phase mixture was stirred vigorously under nitrogen for about 30 minutes. The organic layer was separated, transferred to a reaction flask equipped with a reflux condenser and diluted with 15 ml of absolute ethanol. To this solution was added 0.61 grams (3.0 mmole) of 7-methoxy-1-nitroso-2-naphthol and the resulting reaction mixture refluxed under nitrogen for about 6 hours. The reaction mixture was cooled, the volume reduced under vacuum and 0.29 grams (0.71 mmole) of the product, 9'-methoxy-1,3,3-trimethylspiro [benz[g] indoline-2,3'-[3H] naphth [2,1-b][1,4] oxazine] was obtained as yellow-orange crystals. A solution of the crystals dissolved in ethanol or toluene was colorless. The solution turned blue when irradiated with ultraviolet light.

Provenance & Evidence