Hydrazine hydrate (1:1) → 2-(4-Cyclohexylphenyl)cyclopropanecarbohydrazide

HRID 446765Notes

Reaction equation

HRID 446765 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([O:18]C)=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[NH2:21][NH2:22]>C(O)C>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([NH:21][NH2:22])=[O:18])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58358302Methyl 2-(4-cyclohexylphenyl)cyclopropanecarboxylate

Product 1

HCID 583583052-(4-Cyclohexylphenyl)cyclopropanecarbohydrazideYield 133.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a room temperature solution of methyl 2-(4-cyclohexylphenyl)cyclopropanecarboxylate (150 mg, 0.58 mmol) in ethanol (40 mL) was added hydrazine hydrate (293 mg, 5.85 mmol). The reaction mixture was then heated at 80° C. for 16 h, concentrated in vacuo and the residue dissolved in DCM (50 mL). The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(4-cyclohexylphenyl)cyclopropanecarbohydrazide (200 mg) which was taken on to the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue dissolved in DCM (50 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af181e6f2467420d810b2c15d11e98b8
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Reaction notes

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