1-Tetralone → 1-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 414177Notes

Reaction equation

HRID 414177 reaction equation
C[Si]([C:5]#[N:6])(C)C.[C:7]1(=[O:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1.[Li]>C1COCC1.[I-].[Zn+2].[I-]>[OH:17][C:7]1([CH2:5][NH2:6])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 107241-TetraloneHCID 82115Trimethylsilyl cyanideHCID 3028194Lithium

Product 1

HCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-olYield 73%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Five and one-half g of trimethylsilylcyanide is added to a mixture of 7.3 g of 1-tetralone and 10 mg of zinc iodide. The mixture is stirred at room temperature overnight. It is dissolved in 25 ml dry THF and slowly added to a suspension of 2.3 g of lithium aluminumhydride in 40 ml of THF. Reaction is refluxed for three hours and upon cooling, carefully quenched with water. Precipitate is filtered and aqueous solution is diluted with 100 ml 1N NaOH. It was extracted with ether (3×100 ml), dried over anhydrous MgSO4, filtered, and ether evaporated yielding an oil which solidifies upon standing giving 6.4 g (73%) of (1-hydroxy-1,2,3,4-tetrahydronaphthyl)methylamine.

Workup

  1. customReaction
  2. temperatureis refluxed for three hours
  3. temperatureupon cooling
  4. customcarefully quenched with water
  5. filtrationPrecipitate is filtered
  6. additionaqueous solution is diluted with 100 ml 1N NaOH
  7. extractionIt was extracted with ether (3×100 ml)
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customether evaporated
  11. customyielding an oil which

Sources & evidence

ORD record
ord-329f329a0cdd4493b7078fea42a259cc
Source dataset
uspto-grants-1988_12
Patent number
US04791103

Reaction notes

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