Hydroxyamine hydrochloride → methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamate

HRID 552668Notes

Reaction equation

HRID 552668 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][C:10](=[O:13])[O:11][CH3:12])=[O:8])=[C:5]([CH3:16])[CH:4]=1)=O.Cl.[NH2:18][OH:19]>CO.O>[OH:19][N:18]=[CH:1][C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][C:10](=[O:13])[O:11][CH3:12])=[O:8])=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86654470methyl N-[4-formyl-2-methyl benzoyl]carbamate

Product 1

HCID 86654469methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamateYield 102.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In a solution of 41 mg of methyl N-[4-formyl-2-methyl benzoyl]carbamate in 4 mL of methanol and 1 mL of water, 15 mg of hydroxylamine 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 to obtain 45 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

Sources & evidence

ORD record
ord-8dde2ee248754997a59e3df51e9c064e
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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