Reaction #8316

Reaction equation

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

Solvents

ammonium chloride

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGstirred for 10 min
2. 2
   Washwashed with water (2×50 mL) and brine (50 mL)
3. 3
   Dryingdried with anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe residue is precipitated from ether

Procedure

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.

Source