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

HRID 8220Notes

Reaction equation

HRID 8220 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[N:19][NH2:20])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.[CH2:27]([CH:34]([CH2:39][Br:40])[CH2:35][C:36](Cl)=[O:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CO>ClCCl.[Cl-].[NH4+]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[N:19][NH:20][C:36](=[O:37])[CH2:35][CH:34]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:39][Br:40])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 219929293-Benzyl-4-bromo-butyryl chlorideHCID 73858327(1-Pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine

Product 1

HCID 865926233-Benzyl-4-bromo-butyric acid(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 25517Ammonium ChlorideSolvent

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.

Workup

  1. stirringstirred for 10 min
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is precipitated from ether

Sources & evidence

ORD record
ord-31b2586fc45a4951aff7c78af74ea681
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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