HCID 20682300, compound → HCID 57531883, compound

HRID 906844Notes

Reaction equation

HRID 906844 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[C:5]([F:11])[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 20682300HCID 20682300, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57531883HCID 57531883, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-ethyl-2-fluoro-benzonitrile (1.19 g, 8.0 mmol) in ether (70 mL) was cooled in an ice bath. To the cold, stirred solution was added LiAlH4 (600 mg, 16 mmol). The suspension was then heated to reflux. After several hours at reflux, the suspension was allowed to cool to ambient temperature and was quenched by the careful addition of H2O (600 μL), followed by 15% aqueous NaOH (600 μL), and finally H2O (1.8 mL). The resulting suspension was filtered, and the solids were washed thoroughly with ether. The filtrate was concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzylamine (1.16 g, 95% yield) as a liquid. This material was used for the subsequent amide formation without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.21 (1H, app t, J=7.6 Hz), 6.96-6.86 (2H, m), 3.85 (2H, s), 2.63 (2H, q, J=7.6 Hz), 1.22 (3H, t, J=7.6 Hz).

Workup

  1. temperatureThe suspension was then heated to reflux
  2. temperatureAfter several hours at reflux
  3. customwas quenched by the careful addition of H2O (600 μL)
  4. filtrationThe resulting suspension was filtered
  5. washthe solids were washed thoroughly with ether
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ba6c1352a164d5799531b76e65a1b54
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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