Reacción #797090

Ecuación de reacción

6-bromoquinolin-2-ol

1-iodoheptane

→

title compound

6-bromo-2-(heptyloxy)quinoline

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was evaporated under reduced pressure
2. 2
   Otroto remove most of solvent
3. 3
   Filtraciónfiltered
4. 4
   Lavadowashed with ethyl acetate
5. 5
   ConcentraciónThe filtrate was concentrated

Procedimiento

To a mixture of 6-bromoquinolin-2-ol (352 mg 1.57 mmol) and silver carbonate (863 mg, 3.14 mmol, 2.0 eq.) in toluene (20 mL) was added 1-iodoheptane (355 mg, 1.57 mmol, 1.0 eq.) and stirred for 3 h at 110° C. The reaction mixture was evaporated under reduced pressure to remove most of solvent, then filtered, and washed with ethyl acetate. The filtrate was concentrated to give crude the title compound. The crude product was purified by flash chromatography using PE/EA (20/1) as eluent to give product as a red oil (300 mg, 60%). ESI-MS: 323.8 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ: 7.84-7.83 (m, 2H), 7.70-7.68 (m, 2H), 6.89 (d, 1H), 4.43 (t, 2H), 1.81 (q, 2H), 1.51-1.28 (m, 8H), 0.90 (t, 3H).

Fuente