Hydrochloric Acid → 4-Methoxyisonitrosoacetanilide

HRID 1057440Notes

Reaction equation

HRID 1057440 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 was heated to refulux. The reaction was heated to refulux 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
  3. temperaturewas heated to refulux
  4. temperatureThe reaction was heated
  5. temperaturecooled slowly to room temperature
  6. temperaturecooled in an ice bath
  7. filtrationThe tan precipitate was collected by vacuum filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-76ff7d208cd24b7cb3e32e7b795c817f
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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