7-Methoxy-2-tetralone → 2-Amino-7-methoxytetralin

HRID 2104260Notes

Reaction equation

HRID 2104260 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:20].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH2:20])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 777857-Methoxy-2-tetraloneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 116080152-Amino-7-methoxytetralin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-methoxy-2-tetralone (12.4 g; 70.7 mmol) dissolved in MeOH (350 mL) was added ammonium acetate (82 g; 1.06 mol) and the reaction was stirred for 30 min at room temperature. To the reaction was then added sodium cyanoborohydride (21.5 g; 353 mmol) and the reaction was refluxed for 1 h. Upon completion of the reaction, the reaction was cooled and the solvent removed under reduced pressure. The residue was diluted with EtOAc and 1N NaOH was added to quench the reaction. The aqueous phase was separated and the organic phase washed with H2O, brine, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to yield 7-methoxy-1,2,3,4-tetrahydronapthalen-2-ylamine as a dark oil.

Workup

  1. customUpon completion of the reaction
  2. temperaturethe reaction was cooled
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was diluted with EtOAc and 1N NaOH
  5. additionwas added
  6. customto quench
  7. customthe reaction
  8. customThe aqueous phase was separated
  9. washthe organic phase washed with H2O, brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b939942202a346a4bf0262af2f5eb725
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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