Hydrazine hydrate (1:1) → HCID 178504699, compound

HRID 2119998Notes

Reaction equation

HRID 2119998 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].O.[NH2:24][NH2:25]>C(O)(=O)C.C(O)C>[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([C:9]2[NH:24][N:25]=[C:11]3[C:10]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9879787HCID 9879787, compound

Product 1

HCID 178504699HCID 178504699, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

(E)-1-(4-methanesulfonyl-benzylidene)-3,4-dihydro-1H-naphthalene-2-one (50 mg, 0.16 mmol), hydrazine hydrate (0.0155 ml, 0.32 mmol) were added into ethanol (5.0 ml) and 1-2 drops of acetic acid was added properly. Then, the solution was stirred and refluxed for 48 hours and cooled to room temperature. Afterward, the resulting solution was concentrated under reduced pressure, diluted by adding dichloromethane (10 ml), and then washed with water and the saturated brine. The residue was purified through silica gel column chromatography (eluent: ethylacetate/n-hexane=1/1, v/v). As a result, 35 mg of the present compound (productive yield 68%) was obtained as a brown solid.

Workup

  1. additionwas added properly
  2. temperaturerefluxed for 48 hours
  3. concentrationAfterward, the resulting solution was concentrated under reduced pressure
  4. additiondiluted
  5. additionby adding dichloromethane (10 ml)
  6. washwashed with water
  7. customThe residue was purified through silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-f396c7a6e48a46aca341fa2f344ca22d
Source dataset
uspto-grants-2004_02
Patent number
US06686493B2

Reaction notes

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