Sodium Chloride → HCID 70156897, compound

HRID 2257842Notes

Reaction equation

HRID 2257842 reaction equation
[H-].[Na+].C([O:5][CH2:6][CH3:7])=O.[C:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:23])=[C:16]2[C:21]=1[C:20](=[O:22])C[CH2:18][CH2:17]2)(=[O:10])[CH3:9].[Cl-].[Na+]>C(COC)OC.C(O)C>[C:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:23])=[C:16]2[C:21]=1[C:20](=[O:22])[C:7](=[CH:6][OH:5])[CH2:18][CH2:17]2)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 22449403HCID 22449403, compound

Product 1

HCID 70156897HCID 70156897, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

960 mg of 60% aqueous solution of sodium hydride was added to 8 ml of ethyl formate under ice-cooling, and 5 minutes after the mixture was cooled to room temperature, a solution of 1.43 gm of 8-acetylamino-5-chloro-1-tetralone dissolved in 30 ml of dimethoxyethane was slowly added. After the addition of 0.06 ml of ethanol, the mixture was stirred for 30 minutes. The reaction mixture was poured into 300 ml of 14% aqueous solution of sodium chloride, extracted with ethyl acetate, washed with 10% aqueous solution of citric acid and saturated brine, and dried over anhydrous sodium sulfate. After concentration, ether was added to the residue to collect the precipitate of 1.30 gm of the title compound the by filtration.

Workup

  1. temperaturecooling
  2. additionwas slowly added
  3. extractionextracted with ethyl acetate
  4. washwashed with 10% aqueous solution of citric acid and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration, ether
  7. additionwas added to the residue
  8. customto collect the precipitate of 1.30 gm of the title compound the
  9. filtrationby filtration

Sources & evidence

ORD record
ord-e5b0988b60594b0ab1d2aa2f06d2eca8
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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