Water → 2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-propyloxime

HRID 55987Notes

Reaction equation

HRID 55987 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:22][O:23][CH2:24][CH2:25][CH3:26])[CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O.NN.O>C(O)C>[CH2:24]([O:23][N:22]=[C:9]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)[CH2:10][NH2:11])[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 118071539N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimide

Product 1

HCID 1180715092-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-propyloximeYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 235 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimide in 5 ml of ethanol, 90 mg of hydrazine monohydrate was added and refluxed with heating for 3 hours with stirring. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 20 ml of water and extracted with ethyl acetate (35 ml×2). The resulting organic layers were combined, washed with water (20 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 151 mg of the desired crude product as a brown oil. The oil was used in the next step without further purification.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (35 ml×2)
  5. washwashed with water (20 ml×1)
  6. dry with materialdried over saturated aqueous sodium chloride
  7. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d89d82bde57a4f2da458ae44b5d6ec04
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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