Toluene → HCID 58897780, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, a mixture of 2.79 g (30 mmol) of aniline, 14.5 g (60 mmol) of 4-bromo-1-methoxy-2-methylindane, 20.2 g (180 mmol) of tBuOK, 30 ml of 0.2 M (6.0 mmol) solution of PtBu3 in toluene, and 180 ml toluene, 0.67 g (3.0 mmol) of Pd(OAc)2 was added. This mixture was stirred for 8 hours at 100° C. Then, this mixture was washed with 600 ml of water, and organic layer was separated. The aqueous layer was extracted with 3×150 ml of methyl-tert-butyl ether. To the combined extract, 250 ml of methanol and 150 ml of 10 M HCl were added; and the resulting mixture was refluxed for 7 hours. Sodium bicarbonate (ca. 130 g) was added in small portions until carbon dioxide evolved. The product, N,N-bis(2-methyl-1H-inden-7-yl)-N-phenylamine, was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, l 400 mm, eluant:hexanes-dichloromethane=1:1, vol.) Yield, 7.84 g (80%) of a yellowish oil.

Provenance & Evidence