Methanol → 2-[4-(Trifluoromethyl)phenyl]ethan-1-amine

HRID 856066Notes

Reaction equation

HRID 856066 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)([O-])=O.CO.[OH-].[Na+]>C1COCC1.O>[F:19][C:18]([F:20])([F:21])[C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][NH2:7])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 6882311-(2-Nitro-vinyl)-4-trifluoromethyl-benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amineYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.558 g, 14. 7 mmol) was suspended in THF (10 ml), to which a solution of 1-(2-nitrovinyl)-4-trifluoromethylbenzene (1.596 g, 7.35 mmol) prepared in Reference Example 118 in THF (10 ml) was added dropwise while cooling in an ice-bath, and the mixture was heated under reflux for 2 hours. Methanol was slowly added to the mixture until it no longer foamed. Water (0.6 ml), 15% sodium hydroxide aqueous solution (0.6 ml) and water (1.8 ml) were added in this order, and the insoluble substances were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel with an amine-treated surface (Fuji Silysia; NH-DM1020, solvent; methylene chloride/n-hexane=4/1) to afford 2-(4-trifluoromethylphenyl)ethylamine (0.431 g, yield 31%) as an orange-colored oil.

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling in an ice-bath
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. customthe insoluble substances were removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel with an amine-
  8. additiontreated surface (Fuji Silysia; NH-DM1020, solvent; methylene chloride/n-hexane=4/1)

Sources & evidence

ORD record
ord-7fc5f695342c458aab2efd5bf6e07ed8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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