Hydrazine hydrate (1:1) → HCID 178526599, compound

HRID 45852Notes

Reaction equation

HRID 45852 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=O.O.[NH2:18]N>C(O)C>[N+:13]([C:9]1[CH:8]=[C:7]([C:5]2[CH:4]=[CH:3][NH:2][N:18]=2)[CH:12]=[CH:11][CH:10]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5375681(2E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one

Product 1

HCID 178526599HCID 178526599, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g (11 mmol) of (2E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one were dissolved in 25 ml of ethanol and 2.3 ml of hydrazine hydrate 98% (46 mmol) were added. The resulting solution was refluxed under stirring for 5 hours. The solvent was then evaporated and the crude was dissolved with dichloromethane and washed with water. The organic layer was dried over sodium sulphate and the solvent removed in vacuo. The residue was then triturated with diisopropylether and collected by filtration, giving 2.1 g of the title compound (98%).

Workup

  1. temperatureThe resulting solution was refluxed
  2. customThe solvent was then evaporated
  3. dissolutionthe crude was dissolved with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customthe solvent removed in vacuo
  7. customThe residue was then triturated with diisopropylether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-dd9a691f4ee84b31a5d3a8965a711945
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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