Hydrazine hydrate (1:1) → HCID 118071518, compound

HRID 55983Notes

Reaction equation

HRID 55983 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:22][O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O.NN>C(O)C>[C: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])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131736884HCID 131736884, compound

Product 1

HCID 118071518HCID 118071518, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 162 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]phthalimide in 10 ml of ethanol, 40 mg of hydrazine monohydrate was added, and the mixture was stirred at 80° C. for 1 hour. After completion of the reaction, the solvent was evaporated under reduced pressure, and the reaction mixture was mixed with 30 ml of water and extracted with ethyl acetate (25 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 89 mg of the desired crude product as a colorless oil. The oil was used in the next step without further purification.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionthe reaction mixture was mixed with 30 ml of water
  4. extractionextracted with ethyl acetate (25 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-e779bdfbc84f40e6a68283117fcb73d2
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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