Hydrazine hydrate (1:1) → 3-[3-(Trifluoromethyl)phenyl]propanohydrazide

HRID 452589Notes

Reaction equation

HRID 452589 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](OCC)=[O:12])[CH:6]=[CH:7][CH:8]=1.O.[NH2:19][NH2:20]>C(O)C>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([NH:19][NH2:20])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11849913Ethyl 3-(3-(trifluoromethyl)phenyl)propanoate

Product 1

HCID 686635873-[3-(Trifluoromethyl)phenyl]propanohydrazideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-[3-(trifluoromethyl)phenyl]propionate (9.85 g, 40.0 mmol) and hydrazine monohydrate (9.70 mL, 200 mmol) in ethanol (50 mL) was heated under reflux overnight. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (7.51 g, yield 81%) as colorless crystals.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-94950e67edf540e7a900fbc4978bb23f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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