Hydrazine hydrate (1:1) → HCID 178419935, compound

HRID 34011Notes

Reaction equation

HRID 34011 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=O.O.[NH2:20][NH2:21]>C(O)C.C(OCC)(=O)C>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[NH:20][N:21]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23070192(2-Chlorothiophen-3-yl)-(naphthalen-2-yl)-methanone

Product 1

HCID 178419935HCID 178419935, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.61 g of (2-chlorothiophen-3-yl)-(naphthalen-2-yl)-methanone in 6 mL of ethanol was added 0.12 mL of hydrazine monohydrate at room temperature and heated under reflux for 2 days. The reaction solution was diluted with ethyl acetate, and the organic layer washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resultant crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:30-1:5), to afford 32 mg of the title compound as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 days
  3. washthe organic layer washed successively with saturated aqueous ammonium chloride and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resultant crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:30-1:5)

Sources & evidence

ORD record
ord-be84753c31034ea4b8b82e9f385d878d
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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