Nitromethane → 4-Chloro-2-methyl-1-(2-nitrovinyl)benzene

HRID 1021398Notes

Reaction equation

HRID 1021398 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.Cl.CN.C([O-])(=O)C.[Na+].[N+:19]([CH3:22])([O-:21])=[O:20]>O.ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:22][N+:19]([O-:21])=[O:20])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 27576584-Chloro-2-methylbenzaldehydeHCID 6364545Methylamine hydrochloride

Product 1

HCID 670259694-Chloro-2-methyl-1-(2-nitrovinyl)benzeneYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-2-methylbenzaldehyde (1.56 g, 10.1 mmol), methylamine hydrochloride (0.44 g, 6.5 mmol), and sodium acetate (0.53 g, 6.5 mmol) in nitromethane (4 mL) was vigorously stirred at ambient temperature for 24 hours. The reaction mixture was diluted with water (20 mL) and dichloromethane (40 mL). The organic layer was dried over sodium sulfate and evaporated to afford 4-chloro-2-methyl-1-(2-nitrovinyl)benzene as a light brown solid (1.87 g, 94% yield).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-333207f0cfac4d69b7f15ee12ea9b7fe
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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