Water → 1-(2,4-Dichlorophenyl)propan-2-amine

HRID 389172Notes

Reaction equation

HRID 389172 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]=[C:16]([N+:18]([O-])=O)[CH3:17].O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH2:15][CH:16]([NH2:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 7106762,4-Dichloro-1-(2-nitro-1-propen-1-yl)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 30411751-(2,4-Dichlorophenyl)propan-2-amineYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.33 g, 8.9 mmol) in tetrahydrofuran (20 ml) was added dropwise a solution of 2,4-dichloro-1-(2-nitro-1-propenyl)benzene (1.0 g, 4.3 mmol) in tetrahydrofuran (5 ml) at room temperature. Refluxing started slowly and the mixture was heated under reflux for 1 hr thereafter. The mixture was allowed to cool to room temperature and water (2 ml) was added under cooling in an ice bath. A 1N aqueous sodium hydroxide solution (5 ml) was added, and the insoluble material was removed by filtration through celite. Water was added to the filtrate, and the mixture was extracted with methyl t-butyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give crude [2-(2,4-dichlorophenyl)-1-methylethyl]amine (yield; 0.8 g, 91%).

Workup

  1. temperatureRefluxing
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hr
  4. temperatureunder cooling in an ice bath
  5. customthe insoluble material was removed by filtration through celite
  6. additionWater was added to the filtrate
  7. extractionthe mixture was extracted with methyl t-butyl ether
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-31828cbe13564245a8c1092ce949b1a9
Source dataset
uspto-grants-2013_02
Patent number
US08378114B2

Reaction notes

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