Hydrazine hydrate (1:1) → HCID 54445060, compound

HRID 1354869Notes

Reaction equation

HRID 1354869 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-])=O.O.NN>C1COCC1.CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 739253-(4-Nitrophenyl)prop-2-en-1-ol

Product 1

HCID 54445060HCID 54445060, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 1.5 g (8.37 mmol) of 4-nitrocinnamyl alcohol in THF/methanol (60 mL, 1:1 v/v) was added a catalytic amount of Raney Nickel and hydrazine monohydrate (1.22 mL, 25.1 mmol). The mixture was stirred at room temperature for 3 h, additional hydrazine monohydrate (1.22 mL) being added after 1.5 h. The reaction mixture was filtered over HFLO and concentrated under reduced pressure to 5 mL. Dichloromethane (100 mL) was added and the resultant solution was washed with water, dried over Na2SO4, filtered, and concentrated, which gave 10 (1.24 g, 8.31 mmol, 99%).

Workup

  1. filtrationThe reaction mixture was filtered over HFLO
  2. concentrationconcentrated under reduced pressure to 5 mL
  3. additionDichloromethane (100 mL) was added
  4. washthe resultant solution was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4dfc3e92187541b6b9ed2ff3d4ee7826
Source dataset
uspto-grants-2007_05
Patent number
US07223837B2

Reaction notes

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