Hydrazine hydrate (1:1) → HCID 178420101, compound

HRID 530297Notes

Reaction equation

HRID 530297 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.O.[NH2:15]N>C(O)C>[C:7]1([C:5]2[CH:4]=[CH:3][NH:2][N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5398495(E)-3-Dimethylamino-1-phenyl-propenone

Product 1

HCID 178420101HCID 178420101, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one (2.63 g, 15 mmol) in ethanol (40 ml) was added hydrazine hydrate (1.459 ml, 30.0 mmol). The reaction was heated to 100° C. for 2 hours. Whereupon was cooled to room temperature and ethanol was removed by vacuum. The residue was partitioned between DCM and water. The organic phase was dried over MgSO4 and filtered. After evaporation the crude product was purified by triturating with a mixture of petroleumether and ethyl acetate. (Yield: 1.59 g, 73%).

Workup

  1. temperatureWhereupon was cooled to room temperature
  2. customethanol was removed by vacuum
  3. customThe residue was partitioned between DCM and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customAfter evaporation the crude product
  7. customwas purified
  8. customby triturating with a mixture of petroleumether and ethyl acetate

Sources & evidence

ORD record
ord-6ff3111c2d6d4b42bc3cff12ae976913
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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