Water → HCID 9945157, compound

HRID 1885044Notes

Reaction equation

HRID 1885044 reaction equation
[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[C:10]2/[C:11](=O)[CH2:12][CH2:13][C:14]3[C:19]/2=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])(=O)C.[Na+].Cl.[NH2:29][OH:30].O>C(O)C.C1(C)C=CC=CC=1.ClCCl>[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([C:9]2[O:30][N:29]=[C:11]3[CH2:12][CH2:13][C:14]4[C:19]([C:10]=23)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 9879787HCID 9879787, compound

Product 1

HCID 9945157HCID 9945157, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

(E)-1-(4-methanesulfonyl-benzylidene)-3,4-dihydro-1H-naphthalene-2-one (50 mg, 0.16 mmol) were dissolved in ethanol (2.0 ml) and then anhydrous sodium acetate solution (14.5 mg, 0.18 mmol, saturated with hot acetic acid) and hydroxylamine hydrochloride salt solution (12.2 mg, 0.18 mmole, ethanol 2.0 ml) were added respectively. Then, the solution was heated and refluxed for about 5 hours and cooled to room temperature. Afterward, water and dichloromethane were added, separated to layers, washed with the saturated brine and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure so as to obtain a solid. Again, toluene (5 ml) was poured, refluxed, stirred for 24 hours and cooled to room temperature. After condensing with reduced pressure, the resulting remnant was purified through silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1, v/v). As a result, 35 mg of the present compound (productive yield 71%) was obtained.

Workup

  1. temperatureThen, the solution was heated
  2. temperaturerefluxed for about 5 hours
  3. customseparated to layers
  4. washwashed with the saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe resulting solution was concentrated under reduced pressure so as
  7. customto obtain a solid
  8. temperaturerefluxed
  9. temperaturecooled to room temperature
  10. customAfter condensing with reduced pressure
  11. customthe resulting remnant was purified through silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-0171973dc7fb424a89b2b8eaa565acfd
Source dataset
uspto-grants-2004_07
Patent number
US06768019B2

Reaction notes

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