Hydrazine hydrate (1:1) → HCID 118071493, compound

HRID 55999Notes

Reaction equation

HRID 55999 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:23][O:24][CH3:25])[CH:10]([N:12]2C(=O)C3=CC=CC=C3C2=O)[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O.NN>C(O)C>[CH3:25][O:24][N:23]=[C:9]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)[CH:10]([NH2:12])[CH3:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118071600N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]phthalimide

Product 1

HCID 118071493HCID 118071493, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 810 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyinnino-1-methylethyl]phthalimide in 30 ml of ethanol, 161 mg of hydrazine monohydrate was added and refluxed with heating for 1 hour with stirring. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was mixed with 20 ml of water and extracted with ethyl acetate (30 ml×1). The resulting organic layer was 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 430 mg of the desired crude product as a pale yellow oil. The oil was used in the next step without further purification.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 1 hour
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. additionthe resulting residue was mixed with 20 ml of water
  6. extractionextracted with ethyl acetate (30 ml×1)
  7. washThe resulting organic layer was washed with water (20 ml×1)
  8. dry with materialdried over saturated aqueous sodium chloride
  9. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b161eba2fefa41488e815301c43ec6bb
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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