Hydrochloric Acid → 4-Methoxyisonitrosoacetanilide

HRID 1243452Notes

Reaction equation

HRID 1243452 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>[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

6

Reactant 4

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

Product 1

HCID 67107914-MethoxyisonitrosoacetanilideYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

Chloral hydrate (9.6 g) was dissolved in 200 mL water containing 83 g sodium sulfate. The solution was warmed to 60° C., a solution of 11.4 g hydroxylamine hydrochloride in 50 mL water was added and the mixture was held at 60° C. In a separate flask, 6.4 g 4-anisidine and 4.3 mL concentrated hydrochloric acid in 80 mL of water was warmed to 80° C. The first solution was added to the second and the resulting mixture was refluxed for 2 minutes, 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-hydroximinoacetyl)anisidine.

Workup

  1. customwas held at 60° C
  2. additionThe first solution was added to the second and the resulting mixture
  3. temperaturewas refluxed for 2 minutes
  4. temperaturecooled 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-fbc7c42a089b4ed2a491a7284f6924b8
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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