Hydrochloric Acid → 4-Methoxyisonitrosoacetanilide

HRID 24364

Reaction equation

HRID 24364 reaction equation
Cl.[NH2:2][OH:3].Cl[C:5](Cl)(Cl)[CH:6]([OH:8])O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1.Cl>O>[N:2](=[CH:5][C:6]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)=[O:8])[OH:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 7732P-AnisidineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 67107914-MethoxyisonitrosoacetanilideYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

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

Workup

  1. customwas held at 60° C.
  2. additionThe first solution was then added to the second and the reaction
  3. temperaturewas refluxed for 2 minutes
  4. temperaturecooled in an ice bath
  5. customThe tan precipitate which formed
  6. filtrationwas collected by vacuum filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-deec456113a2417395df3df26c07fc19
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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