Nitric Acid → HCID 22119059, compound

HRID 1419115Notes

Reaction equation

HRID 1419115 reaction equation
Cl.[CH3:2][NH:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][C:12](=[O:14])[CH3:13])=[C:6]([CH3:15])[C:5]=1[CH3:16].[N+:17]([O-])([OH:19])=[O:18].C(=O)([O-])O.[Na+]>>[CH3:2][NH:3][C:4]1[C:9]([N+:17]([O-:19])=[O:18])=[C:8]([CH3:10])[C:7]([O:11][C:12](=[O:14])[CH3:13])=[C:6]([CH3:15])[C:5]=1[CH3:16]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 22119055HCID 22119055, compound

Product 1

HCID 22119059HCID 22119059, compound

Procedure

4.3 g of N-methyl-4-acetoxy-2,3,5-trimethylaniline hydrochloride (prepared as described in Preparation 17) were added to ice-cooled concentrated aqueous nitric acid, and the resulting mixture was stirred, whilst ice-cooling, for 10 minutes and then at room temperature for 10 minutes. At the end of this time, the reaction mixture was poured into ice-water and the aqueous mixture was neutralized by the addition of sodium hydrogencarbonate, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, after which 50 ml of diisopropyl ether and 50 ml of hexane were added to the residue. The mixture was then agitated ultrasonically for 5 minutes. Insoluble precipitates were triturated with a 1:1 by volume mixture of diisopropyl ether and hexane. The resulting crystals were collected by filtration, after which they were washed with a 1:1 by volume mixture of diisopropyl ether and hexane to give 2.76 g of the title compound, melting at 143°-146° C.

Workup

  1. temperaturecooling, for 10 minutes
  2. extractionafter which it was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. additionafter which 50 ml of diisopropyl ether and 50 ml of hexane were added to the residue
  7. stirringThe mixture was then agitated ultrasonically for 5 minutes
  8. customInsoluble precipitates
  9. customwere triturated with a 1:1 by volume mixture of diisopropyl ether and hexane
  10. filtrationThe resulting crystals were collected by filtration
  11. washafter which they were washed with a 1:1 by volume mixture of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-539d45b60aee47adb437207e8fdc1f48
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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