Hydrochloric Acid → 2-[2-(4-Pyridyl)ethenyl]aniline

HRID 1741013Notes

Reaction equation

HRID 1741013 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[CH:4][CH:3]=1>C(O)C>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543300572-[2-(4-Pyridyl)ethenyl]-1-nitrobenzene

Product 1

HCID 2913412-[2-(4-Pyridyl)ethenyl]anilineYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a mixture of concentrated hydrochloric acid (14 ml) and ethanol (14 ml) was dissolved 2.87 g of 2-[2-(4-pyridyl)ethenyl]-1-nitrobenzene. To this solution was added a solution of stannous chloride dihydrate (8.59 g) in ethanol (25 ml) gradually dropwise under ice-cooling and the mixture was stirred at room temperature for 5 hours. After the solvent was evaporated off under reduced pressure, the residue was made basic with 30% aqueous sodium hydroxide solution and extracted with chloroform. The extract was dehydrated over anhydrous magnesium sulfate and the solvent was evaporated off to provide 2.2 g of the title compound as yellow solid. This product was used as a starting material without purification.

Workup

  1. temperaturecooling
  2. customAfter the solvent was evaporated off under reduced pressure
  3. extractionextracted with chloroform
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-502745d2bee84f92a5990eabe642ba8d
Source dataset
uspto-grants-1999_10
Patent number
US05972976

Reaction notes

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