Sulfuric Acid → 2-(2-Fluoro-4-methoxyphenyl)ethanamine

HRID 890377Notes

Reaction equation

HRID 890377 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH:16]=[CH:17][N+:18]([O-])=O.OS(O)(=O)=O>C1COCC1>[F:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][CH2:17][NH2:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydride2×HCID 670319522-Fluoro-4-methoxy-1-(2-nitro-vinyl)-benzene

Product 1

HCID 221750092-(2-Fluoro-4-methoxyphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (3.5 equivalents) was suspended in THF and brought to reflux. 2-fluoro-4-methoxy-1-(2-nitro-vinyl)-benzene (1 equivalent) was dissolved in THF and added dropwise to the LiAlH4. The reaction was allowed to proceed at reflux overnight. The reaction was then cooled in an ice bath and H2SO4 was added dropwise. The reaction was extracted with ether. The ether fractions were discarded. The aqueous layer was adjusted to pH 12 with 5% NaOH and extracted with ether (3×). Combined ether fractions were washed with brine and dried over Na2SO4. Solvent was removed to yield 2-(2-fluoro-4-methoxy-phenyl)-ethylamine as an oil, which was used without further purification.

Workup

  1. temperatureto reflux
  2. temperatureat reflux overnight
  3. temperatureThe reaction was then cooled in an ice bath
  4. extractionThe reaction was extracted with ether
  5. extractionextracted with ether (3×)
  6. washCombined ether fractions were washed with brine
  7. dry with materialdried over Na2SO4
  8. customSolvent was removed

Sources & evidence

ORD record
ord-ac01c606f2ca4d43a8d8b7f566de2243
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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