Water → 2-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime

HRID 56064Notes

Reaction equation

HRID 56064 reaction equation
[Cl:1][C:2]1[C:3]([C:14](=[N:27][O:28][CH3:29])[CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:7]=1.O.NN.O>C(O)C>[CH3:29][O:28][N:27]=[C:14]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[CH:5][N:4]=1)[CH2:15][NH2:16]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 118071586HCID 118071586, compound

Product 1

HCID 1180716032-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloximeYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 790 mg of N-[2-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-2-(methoxyimino)ethyl]phthalimide in 10 ml of ethanol, 187 mg of hydrazine monohydrate was added and refluxed with heating for 1 hour with stirring. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 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 446 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 1 hour
  3. customAfter completion of the reaction
  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-f1e6c788e34b42479ad599e73b580c69
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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