1-Naphthylamine → N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amine

Temperatur

90 °C

Under nitrogen, 12 mL of dehydration xylene was added to a mixture of 3.7 g (10 mmol) of 3-iodo-9-phenylcarbazole, 1.6 g (5 mmol) of 1-aminonaphthalen, 60 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), 200 μL (0.5 mmol) of tri(t-butyl)phosphine (49 wt % hexane solution), 3 g (30 mmol) of t-butoxysodium (abbreviation: t-BuONa). This was stirred while heating at 90° C. under a nitrogen atmosphere for 7 hours. After the termination of the reaction, this suspension was added with about 200 mL of hot toluene and was filtered through florisil®, alumina, and celite. The obtained filtrate was concentrated and this residue was separated by silica gel column chromatography (toluene:hexane=1:1). When an obtained solid was recrystallized with a mixture of ethyl acetate and hexane, 1.5 g of 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (PCN) that was a target substance and was cream-colored powder was obtained in a yield of 79% (Synthesis Scheme (g-1)).

1. customAfter the termination of the reaction
2. filtrationwas filtered through florisil®, alumina, and celite
3. concentrationThe obtained filtrate was concentrated
4. customthis residue was separated by silica gel column chromatography (toluene:hexane=1:1)
5. customWhen an obtained solid was recrystallized with a mixture of ethyl acetate and hexane, 1.5 g of 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (PCN) that
6. customwas obtained in a yield of 79% (Synthesis Scheme (g-1))

ORD-Eintrag

ord-dfb7ccf6abd1414dbc18e28aa96edc65

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08686628B2