Hydroxyamine hydrochloride → HCID 87247295, compound

HRID 2367144Notes

Reaction equation

HRID 2367144 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:13][OH:14]>C(O)C>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4](/[C:8](=[N:13]\[OH:14])/[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 15313764177942-43-7

Product 1

HCID 87247295HCID 87247295, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(3-Chloro-2-methyl-phenyl)-ethanone (390 mg, 2.3 mmol) was dissolved in ethanol (6 ml) and hydroxylamine hydrochloride (433 μL, 10.4 mmol) was added. The mixture was stirred at 80° C. for 1.5 hours. Reaction mixture was concentrated in vacuo and partitioned between water and ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined organic portions were washed with brine, dried over sodium sulfate and concentrated in vacuo to give (1Z)-1-(3-chloro-2-methylphenyl)ethanone oxime as a yellow oil (383 mg, 2.08 mmol, 90% yield). 1H NMR (400 MHz, CDCl3): 6.95-7.37 (m, 3H), 2.36 (s, 3H), 2.26 (s, 1H), 2.21 (s, 3H); MS (EI) for C9H10ClNO: 184 (MH+).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous portion was extracted with ethyl acetate
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c422590902784024b0eecc5893027550
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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