Reacción #8316

Ecuación de reacción

methanol

3-benzyl-4-bromo-butyryl chloride

(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine

pyridine

→

title compound

3-Benzyl-4-bromo-butyric acid (1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide

Disolventes

ammonium chloride

dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 10 min
2. 2
   Lavadowashed with water (2×50 mL) and brine (50 mL)
3. 3
   Secadodried with anhydrous sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue is precipitated from ether

Procedimiento

A solution of (1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine (2.25 g, 8.40 mmol) in anhydrous dichloromethane (100 mL) and pyridine (1.81 mL, 22.4 mmol) is cooled to −78° C., treated with a solution of 3-benzyl-4-bromo-butyryl chloride (2.1 g, 7.8 mmol) in dichloromethane (10 mL), and stirred for 2 h. The mixture is treated with methanol (3 mL), stirred for 10 min, and diluted with saturated ammonium chloride solution (30 mL). The mixture is diluted with dichloromethane (300 mL), washed with water (2×50 mL) and brine (50 mL), dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue is precipitated from ether to yield the title compound, 2.3 g (60%), as a pale yellowish solid.

Fuente