Acetic Acid → HCID 9859076, compound

HRID 1045652Notes

Reaction equation

HRID 1045652 reaction equation
[C:1]1(=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[N:11]O.[C:14](O)(=[O:16])[CH3:15]>C(OC(=O)C)(=O)C.[Zn]>[O:13]=[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:11][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 6813148HCID 6813148, compound

Product 1

HCID 9859076HCID 9859076, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Zinc powder (24 g, 367 mmol) was added to a solution of 3,4-dihydro-[1,2]naphthoquinone 2-oxime (21.5 g, 123 mmol) in acetic acid (200 mw) and acetic anhydride (150 ml), and the solution was stirred at room temperature for 12 hours. After filtration and removal of the solvents under reduced pressure, the residue was partitioned between water and chloroform. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was washed with ethyl acetate and dried to afford N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (16.5 g, 81 mmol, 66%) as brown crystals.

Workup

  1. filtrationAfter filtration and removal of the solvents under reduced pressure
  2. customthe residue was partitioned between water and chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of the solvent
  6. washthe residue was washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-14810c1b78c149e2ad3146ee4c605435
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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