Water → 2-amino-1-(2,4-dichlorophenyl)ethanone-O-methyloxime

HRID 55974Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:22][O:23][CH3:24])[CH2:10][N:11]1C(=O)C2=CC=CC=C2C1=O.O.NN.O>C(O)C>[CH3:24][O:23][N:22]=[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:10][NH2:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To 316 mg of N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]phthalimide in 10 ml of ethanol, 108 mg of hydrazine monohydrate was added, and the mixture was stirred at 60° C. for 2 hours. 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 (40 ml×1). The resulting organic layer was dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 170 mg of the desired crude product as a colorless oil. The oil was used in the next step without further purification.

Workup

customAfter completion of the reaction
temperatureto cool to room temperature
extractionextracted with ethyl acetate (40 ml×1)
dry with materialThe resulting organic layer was dried over saturated aqueous sodium chloride
customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-833bc5b68906462099080f574e29eff0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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