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

HRID 55979Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:9](=[N:22][O:23][CH2:24][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.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])[CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

To 3.00 g of N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]phthalimide in 30 ml of ethanol, 793 mg of hydrazine monohydrate was added, and the mixture was stirred at 70° C. for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 100 ml of water and extracted with ethyl acetate (100 ml×2). The resulting organic layers were combined, washed with water (100 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.62 g of the desired crude product as a brown 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 (100 ml×2)
washwashed with water (100 ml×1)
dry with materialdried over saturated aqueous sodium chloride
customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-10f04baf2a734acaa3e94b8806f148c7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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