Acetone → Spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine], 6'-(2,3-dihydro-1H-indol-1-yl)-1,3-dihydro-1,3,3-trimethyl-

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A mixture of 1-nitroso-2-naphthol (17.3 g; 0.10 mol) and indoline (23.8 g; 0.20 mol) in trichloroethylene (150 ml) was heated under reflux for 10 min. A solution of 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (17.3 g; 0.1 mol) in trichloroethylene (100 ml) was added in one batch and the resulting mixture heated under reflux for 1 h. The solution was evaporatedand the oily residue treated with acetone to yield 1,3-Dihydro-1,3,3-trimethyl-6'-(2,3-dihydroindol-1-yl)spiro [2H-indole-2,3'-3H-naphtho[2,1-b][1,4]oxazine] as a yellow solid (4.44 g; 10%).

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