Hydrochloric Acid → 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide

HRID 1157441Notes

Reaction equation

HRID 1157441 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:16][OH:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[CH3:27].Cl>O>[OH:17][N:16]=[CH:2][C:3]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[C:21]([CH3:27])[CH:22]=1)=[O:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 672973-Methyl-4-methoxybenzenamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 713346932-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloral hydrate (11.5 g, 70 mmol) and anhydrous sodium sulfate (60 g, 422 mmol) were added to vigorously stirred water (300 mL). A slurry prepared by mixing hydroxylamine hydrochloride (23.0 g, 331 mmol) and 4-methoxy-3-methylphenylamine (10.0 g, 73 mmol) with aqueous hydrochloric acid (2.4 M, 250 mL) was added to the above mixture. The resulting mixture was refluxed for 20 min and then allowed to stand at room temperature for 16 h. A precipitate formed and was collected by filtration. The solid was washed with water and dried to yield 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide (6.7 g, 32 mmol, 44%)

Workup

  1. customA slurry prepared
  2. additionwas added to the above mixture
  3. temperatureThe resulting mixture was refluxed for 20 min
  4. customA precipitate formed
  5. filtrationwas collected by filtration
  6. washThe solid was washed with water
  7. customdried

Sources & evidence

ORD record
ord-0d0120445368487699f1eaf50d4de750
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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