Hydrochloric Acid → 4-Methoxyisonitrosoacetanilide

HRID 24318

Reaction equation

HRID 24318 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.Cl.[NH2:9][OH:10].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.Cl>O.S([O-])([O-])(=O)=O.[Na+].[Na+]>[N:9](=[CH:2][C:3]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)=[O:5])[OH:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 7732P-AnisidineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 67107914-MethoxyisonitrosoacetanilideYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 24436Sodium SulfateSolvent

Conditions

Temperature
60 °C

Procedure

Chloral hydrate (9.6 g) was dissolved in 200 mL of water containing 83 g of sodium sulfate. The solution was warmed to 60° C., a solution of 11.4 g of hydroxylamine hydrochloride in 50 mL of water was added and the mixture was held at 60° C. In a separate flask, 6.4 g of 4-anisidine and 4.3 mL of concentrated hydrochloric acid in 80 mL of water was warmed to 80° C. The first solution was added to the second and the mixture refluxed for 2 minutes after which it was cooled slowly to room temperature and then cooled in an ice bath. The tan precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 8.6 g (85% yield) of N-(2-hydroximino-acetyl)anisidine.

Workup

  1. customwas held at 60° C
  2. additionThe first solution was added to the second and the mixture
  3. temperaturerefluxed for 2 minutes after which it
  4. temperaturewas cooled slowly to room temperature
  5. temperaturecooled in an ice bath
  6. filtrationThe tan precipitate was collected by vacuum filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6aec756dbaea426a847093dad6f4cd85
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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