Aluminium lithium hydride → 2,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamine

HRID 1447034Notes

Reaction equation

HRID 1447034 reaction equation
[F:1][C:2]([C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[N:6]O)([F:4])[F:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OC(C)C)(C)C>[F:15][C:14]([F:16])([F:17])[C:10]1[CH:9]=[C:8]([CH:5]([NH2:6])[C:2]([F:1])([F:3])[F:4])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71375430N-{2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethylidene}hydroxylamine

Product 1

HCID 438251722,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

2.5 g (3-trifluoromethyl phenyl) trifluoromethyl Ketoxime are suspended in 40 ml isopropyl ether and to this suspension 4 g lithium aluminum hydride are added. The mixture is heated to reflux for 3 hours then cooled. The excess of reagent is destroyed by cautious addition of an aqueous solution of tartaric acid. The mixture is made basic by adding sodium hydroxide and the ethereal phase is separated. The aqueous phase is further extracted with isopropyl ether; the organic solutions are united, washed with water, dried and evaporated off under reduced pressure.

Workup

  1. additionare added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 3 hours
  4. temperaturethen cooled
  5. customThe excess of reagent is destroyed by cautious addition of an aqueous solution of tartaric acid
  6. additionby adding sodium hydroxide
  7. customthe ethereal phase is separated
  8. extractionThe aqueous phase is further extracted with isopropyl ether
  9. washwashed with water
  10. customdried
  11. customevaporated off under reduced pressure

Sources & evidence

ORD record
ord-2f958577a4294ea4898272d7b0a01615
Source dataset
uspto-grants-1982_02
Patent number
US04315019

Reaction notes

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