Acetic Anhydride → Acetamide, N-(1,2,3,4-tetrahydro-4-phenyl-2-naphthalenyl)-

HRID 1460632Notes

Reaction equation

HRID 1460632 reaction equation
Cl.[C:2]1([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH:10]([NH2:18])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])(=[O:21])[CH3:20].[Na+].C(OC(=O)C)(=O)C>C(OCC)(=O)C.O>[C:2]1([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH:10]([NH:18][C:19](=[O:21])[CH3:20])[CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 45260987HCID 45260987, compound

Product 1

HCID 10220953Acetamide, N-(1,2,3,4-tetrahydro-4-phenyl-2-naphthalenyl)-Yield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 180 mg (0.80 mmol) of 4-phenyl-2-aminotetraline HCl in 3.5 ml ethyl acetate and 2.0 ml water, was added 360 mg of sodium acetate. To this mixture 0.6 ml of acetic anhydride was then added and the mixture was stirred for 24 hrs. The addition of 2 ml of water resulted in the formation of two layers. After separation, the water layer was extracted twice with ethyl acetate. The combined organic layers were washed 3 times with a saturated solution of sodium bicarbonate and once with a saturated solution of sodium chloride. After drying over magnesium sulfate, the organic solution was evaporated under reduced pressure to yield 4-phenyl-2-acetamidotetralin as a white solid (170 mg, 79%).

Workup

  1. customresulted in the formation of two layers
  2. customAfter separation
  3. extractionthe water layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed 3 times with a saturated solution of sodium bicarbonate
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe organic solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-abacf55fdafc44d290373d267b861392
Source dataset
uspto-grants-1991_12
Patent number
US05071875

Reaction notes

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