Aluminium lithium hydride → 2-(3-Ethoxyphenyl)ethan-1-amine

HRID 1784414Notes

Reaction equation

HRID 1784414 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][N+:18]([O-])=O)[CH:11]=1)[CH3:8]>C1COCC1>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][NH2:18])[CH:13]=[CH:14][CH:15]=1)[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 688305181-Ethoxy-3-(2-nitroethyl)benzene

Product 1

HCID 27587652-(3-Ethoxyphenyl)ethan-1-amineYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiAlH4 (1M in THF, 13 mL) was added dropwise a solution of 1-ethoxy-3-(2-nitro-ethyl)-benzene (0.5 g, 2.6 mmol) in THF (8 mL). The mixture was refluxed for two hours before allowing to cool and adding dropwise to rochelles salt. The mixture was extracted with ethyl acetate, dried with sodium sulfate and evaporated to dryness. The resulting yellow oil was purified by chromatography on silica, eluting with 3 to 15% MeOH/NH3 in dichloromethane, yielding the subtitled compound as a yellow oil (0.23 g).

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. temperatureto cool
  3. additionadding dropwise to rochelles salt
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness
  7. customThe resulting yellow oil was purified by chromatography on silica
  8. washeluting with 3 to 15% MeOH/NH3 in dichloromethane

Sources & evidence

ORD record
ord-36b41ebb896b47749e4443362d11c61f
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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