Acetic Acid → 2,8-Diacetylamino-1-tetralone

HRID 355946Notes

Reaction equation

HRID 355946 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[C:13](=[O:15])[C:12](=[N:16]O)[CH2:11][CH2:10]2)(=[O:3])[CH3:2].[C:18](O)(=[O:20])[CH3:19]>C(OC(=O)C)(=O)C.[Zn]>[C:18]([NH:16][CH:12]1[CH2:11][CH2:10][C:9]2[C:14](=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][CH:8]=2)[C:13]1=[O:15])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 867509568-Acetylamino-2-hydroxyimino-1-tetralone

Product 1

HCID 120472982,8-Diacetylamino-1-tetralone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

1 gm of zinc powder was added to a solution of 300 mg of the compound prepared in (2) above dissolved in a mixed solvent of 10 ml of acetic acid and 10 ml of acetic anhydride, and the mixture was stirred for 40 minutes at room temperature. Insoluble substances were removed by filtration and filtrate was concentrated. The residue was recrystallized in ethyl acetate and hexane to obtain 263 mg of the title compound.

Workup

  1. customInsoluble substances were removed by filtration and filtrate
  2. concentrationwas concentrated
  3. customThe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-4f6593ea681143ac8b6e501516b36baf
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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