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

HRID 988976Notes

Reaction equation

HRID 988976 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]=[CH:11][N+:12]([O-])=O.OS(O)(=O)=O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][NH2:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 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

LiAIH4 (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 LiAIH4. 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. additionadded dropwise to the LiAIH4
  3. temperatureat reflux overnight
  4. temperatureThe reaction was then cooled in an ice bath
  5. extractionThe reaction was extracted with ether
  6. extractionextracted with ether (3×)
  7. washCombined ether fractions were washed with brine
  8. dry with materialdried over Na2SO4
  9. customSolvent was removed

Sources & evidence

ORD record
ord-b64cf9dd301b4c80a903ec70838dd999
Source dataset
uspto-grants-2003_10
Patent number
US06638927B2

Reaction notes

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