Potassium Acetate → N-[2-(7-Methoxy-1-naphthyl)-2-oxoethyl]acetamide

HRID 551779Notes

Reaction equation

HRID 551779 reaction equation
[OH:1][CH:2]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH2:3][NH:4][C:5](=[O:7])[CH3:6].C([O-])(=O)C.[K+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][CH:9]=[C:8]2[C:2](=[O:1])[CH2:3][NH:4][C:5](=[O:7])[CH3:6])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 44359309HCID 44359309, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 44541672N-[2-(7-Methoxy-1-naphthyl)-2-oxoethyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound obtained in Step F (7.7 mmol) is dissolved in 200 ml of anhydrous dichloromethane. The resulting solution is added to a suspension of potassium acetate (0.23 g) and pyridinium chlorochromate (11.6 mmol) in 50 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 2 hours. It is then filtered over Celite. The filtrate is washed with water, decolourised on vegetable carbon and evaporated under reduced pressure. The residue obtained is triturated in diethyl ether, filtered off under suction and recrystallised from diisopropyl ether to yield the title product in the form of a white solid.

Workup

  1. filtrationIt is then filtered over Celite
  2. washThe filtrate is washed with water
  3. customevaporated under reduced pressure
  4. customThe residue obtained
  5. customis triturated in diethyl ether
  6. filtrationfiltered off under suction
  7. customrecrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-3d8f6233a57d498eb66559249da66e91
Source dataset
uspto-grants-2011_05
Patent number
US07947852B2

Reaction notes

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