Water → 2-Acetamido-8-methoxytetralin

HRID 2257826Notes

Reaction equation

HRID 2257826 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.C([BH3-])#[N:15].[Na+].[C:18]([O-:21])(=O)[CH3:19].[NH4+].O>CO>[C:18]([NH:15][CH:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)(=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 41360218-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 30189202-Acetamido-8-methoxytetralinYield 126.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.18 gm of 8-methoxy-2-tetralone [described in J. Chem. Soc. 2636 (1965)] dissolved in 100 ml of methanol, were added 560 mg of sodium cyanoborohydride and 4.86 gm of ammonium acetate, and the mixture was stirred for 89 hours at room temperature. The reaction mixture was ice-cooled and adjusted to below pH 1, followed by the addition of 500 ml of water. After washing with ether, the water layer was adjusted to greater than pH 10 with potassium hydroxide and extracted with ether. The extract was dried over anhydrous magnesium sulfate, and the residue obtained by removing the solvent was dissolved in 50 ml of methylene chloride. 2 ml of pyridine and 2.4 ml of acetic anhydride were added to the solution, followed by stirring at room temparature for 1 hour. The reaction mixture was washed with 10% aqueous solution of hydrochloric acid, saturated aqueous solution of sodeum bicarbonate, and saturated brine in this order, and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was ctystallized in ethyl acetate and hexane to produce 2.47 gm of the title compound.

Workup

  1. temperaturecooled
  2. washAfter washing with ether
  3. extractionextracted with ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe residue obtained
  6. customby removing the solvent
  7. dissolutionwas dissolved in 50 ml of methylene chloride
  8. addition2 ml of pyridine and 2.4 ml of acetic anhydride were added to the solution
  9. stirringby stirring at room temparature for 1 hour
  10. washThe reaction mixture was washed with 10% aqueous solution of hydrochloric acid, saturated aqueous solution of sodeum bicarbonate, and saturated brine in this order
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customAfter removal of the solvent

Sources & evidence

ORD record
ord-f0c527cb6ffb45c28b4230b0c3beeaff
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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