Reaction #69603

Reaction equation

8

1-[Bromo(phenyl)methyl]naphthalene

2-methyl-8-aminoquinoline

8

1-[Bromo(phenyl)methyl]naphthalene

→

title compound A5

Yield 12.0%

2-Methyl-N-[1-naphthyl(phenyl)methyl]quinolin-8-amine

Yield 12.0%

Solvents

triethylamine

triethylamine

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting mixture was stirred for additional 2 hr at 120° C
2. 2
   OtherFinally, the product was isolated

Procedure

A mixture of 2.05 g (13.0 mmol) of 2-methyl-8-aminoquinoline, 2.53 g (25 mmol) of triethylamine and 7.43 g (25 mmol) of 8 was stirred for 2 hr at 120° C. One more portion of 2.53 g of triethylamine as well as 7.43 g of 8 was added. The resulting mixture was stirred for additional 2 hr at 120° C. Finally, the product was isolated using flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-ethyl acetate=20:1, vol.) to give 0.56 g (12%) of the title compound A5.

Source