Hydroxyamine hydrochloride → HCID 136337818, compound

HRID 1187996Notes

Reaction equation

HRID 1187996 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][CH:10]=[N:11][O:12][CH3:13])=[O:8])=[C:5]([CH3:16])[CH:4]=1)=O.Cl.[OH:18][NH2:19]>CO.O>[OH:18][N:19]=[CH:1][C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][CH:10]=[N:11][O:12][CH3:13])=[O:8])=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 1363378174-formyl-N-(methoxyiminomethyl)-2-methyl benzoic acid amide

Product 1

HCID 136337818HCID 136337818, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In a solution of 64 mg of 4-formyl-N-(methoxyiminomethyl)-2-methyl benzoic acid amide in 4 mL of methanol and 1 mL of water, 30 mg of hydroxyamine hydrochloride was added at room temperature with stirring, and continued to stir at the same temperature for 1.5 hour. After the completion of the reaction, 10 mL of water was added in the reaction mixture, and extracted with ethyl acetate (10 mL×2). The combined organic phases were dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (1:1) to obtain 70 mg of the aimed product as white crystal.

Workup

  1. stirringto stir at the same temperature for 1.5 hour
  2. additionwas added in the reaction mixture
  3. extractionextracted with ethyl acetate (10 mL×2)
  4. dry with materialdried over saturated sodium chloride aqueous solution
  5. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  6. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-4f749600d82b4328ba4f0135108c9089
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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