Hydrochloric Acid → 5,6,7,8-Tetrahydro-2-naphthylamine

HRID 260679Notes

Reaction equation

HRID 260679 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-])=O.O.Cl.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 384457-Nitro-1-tetraloneHCID 178418361HCID 178418361, compound

Product 1

HCID 751935,6,7,8-Tetrahydro-2-naphthylamineYield 86,687.797%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Nitrotetralone (20.0 9, 0.105 mmol) was dissolved in 400 ml of ethanol, and 40 ml of water, 10 ml of concentrated HCl, and 4.0 g of 10% palladium on carbon were added. The reaction mixture was reacted with hydrogen at 30-40 psi for 16 hours. Following hydrogenation, the reaction mixture was filtered and the solvents were evaporated, yielding white crystals. The crystals were washed with acetone, dissolved in cold 10% NaOH, and extracted with EtOAc (3 x). The combined organic layers were washed with water, dried over Na2SO4, filtered and evaporated, to give 2-amino-5,6,7,8-tetrahydronaphthalene (13.4 g, 87.1% yield) as a brown oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe solvents were evaporated
  3. customyielding white crystals
  4. washThe crystals were washed with acetone
  5. dissolutiondissolved in cold 10% NaOH
  6. extractionextracted with EtOAc (3 x)
  7. washThe combined organic layers were washed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-280fa59257694b5ea051f2cc2b3a6855
Source dataset
uspto-grants-1996_06
Patent number
US05530005

Reaction notes

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