2-(4-tert-Butylphenyl)cyclopropanecarbohydrazide → 2-(4-tert-butylphenyl)-N-[(E)-1-isoquinolin-5-ylethylideneamino]cyclopropane-1-carboxamide

HRID 446769

Reaction equation

HRID 446769 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([NH:16][NH2:17])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:18]1[C:27]2[C:22](=[C:23]([C:28](=O)[CH3:29])[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][N:19]=1>ClCCCl.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([NH:16]/[N:17]=[C:28](/[C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:22]=2[CH:21]=[CH:20][N:19]=[CH:18]3)\[CH3:29])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5891992-(4-tert-Butylphenyl)cyclopropanecarbohydrazideHCID 204934691-(Isoquinolin-5-yl)ethan-1-one

Product 1

HCID 461862572-(4-tert-butylphenyl)-N-[(E)-1-isoquinolin-5-ylethylideneamino]cyclopropane-1-carboxamideYield 45.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A solution of 2-(4-tert-butylphenyl)cyclopropanecarbohydrazide (200 mg, 0.86 mmol) and 1-(isoquinolin-5-yl)ethanone (147 mg, 0.86 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 2 h. The reaction mixture was then diluted with water (5 mL) and the organic layer was separated, washed brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude material was purified via silica gel column chromatography to afford (E)-2-(4-tert-butylphenyl)-N′-(1-(isoquinolin-5-yl)ethylidene)cyclopropanecarbohydrazide (150 mg, 45%) as an off-white solid.

Workup

  1. customthe organic layer was separated
  2. washwashed brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-293c0aa1fa3140b89398af1687bb6c1c
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Linked notes

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