Sulfuric acid magnesium salt (1:1) → 2-(4-(4-Methylpyridin-2-yl)-2-nitrobenzylidene)propionitrile

HRID 1060014Notes

Reaction equation

HRID 1060014 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:26]([CH3:29])[C:27]#[N:28])C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[C:26]([CH3:29])[C:27]#[N:28])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 136931782-(Triphenylphosphoranylidene)propanenitrileHCID 186675944-(4-Methylpyridin-2-yl)-2-nitrobenzaldehyde

Product 1

HCID 536430862-(4-(4-Methylpyridin-2-yl)-2-nitrobenzylidene)propionitrileYield 94.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-(4-methylpyridin-2-yl)-2-nitrobenzaldehyde (203 mg) and 2-(triphenylphosphoranylidene)propionitrile (0.45 g) in toluene (10 ml) was refluxed for 3 hours. After cooling, to the reaction mixture were added magnesium sulfate and silica gel (10 g), and the suspension was stirred for 30 minutes. The solid was removed by filtration and washed with toluene (10 ml) three times. The combined filtrate was evaporated under reduced pressure to give 2-(4-(4-methylpyridin-2-yl)-2-nitrobenzylidene)propionitrile (221 mg) as a mixture of regioisomers.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. customThe solid was removed by filtration
  4. washwashed with toluene (10 ml) three times
  5. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5b6968ef04c480daa596c4388ac74e5
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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