6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-one → 6-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine

HRID 898863Notes

Reaction equation

HRID 898863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.C([O-])(=O)C.[NH4+:18].C([BH3-])#[N:20].[Na+]>CO>[NH4+:20].[OH-:2].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH2:18])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 199076-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamineYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-methoxy-2-tetralone (10.0 g; 56.7 mmol) dissolved in MeOH (400 mL) is added ammonium acetate (65 g; 0.84 mol) and the reaction was stirred for 30 min. at RT. To the reaction is then added sodium cyanoborohydride (17.8 g; 0.28 mol) and the reaction was refluxed for 1-2 h. The reaction is cooled, the solvent removed under reduced pressure, the residue diluted with EtOAc and 1N NaOH added to quench the reaction. The aqueous phase is separated and the organic phase washed with H2O, brine, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to afford a crude residue which was purified by flash chromatography (SiO2) eluting with CH2Cl2/MeOH:NH4OH (10%) to provide 5.0 g (50%) of 6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine as a dark oil. To a solution of titled compound in ether (100 mL) cooled to 0° C. is bubbled HCl (g) until the solution is saturated.

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent removed under reduced pressure
  3. additionthe residue diluted with EtOAc and 1N NaOH
  4. additionadded
  5. customto quench
  6. customthe reaction
  7. customThe aqueous phase is separated
  8. washthe organic phase washed with H2O, brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure
  12. customto afford a crude residue which
  13. customwas purified by flash chromatography (SiO2)
  14. washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-b8834248ca104c3dabba861f7ddcd1fa
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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