Nitric Acid → HCID 10813284, compound

HRID 1439930Notes

Reaction equation

HRID 1439930 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:6][C:5]2[C:7]([CH3:28])=[CH:8][C:9]([CH3:27])=[C:10]([NH:11][C:12](=[O:26])[C:13]([CH3:25])([CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[O:3]1.[N+:30]([O-])([OH:32])=[O:31]>C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>[CH3:29][C:2]1([CH3:1])[CH2:6][C:5]2[C:7]([CH3:28])=[C:8]([N+:30]([O-:32])=[O:31])[C:9]([CH3:27])=[C:10]([NH:11][C:12](=[O:26])[C:13]([CH3:25])([CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 10573139HCID 10573139, compound

Product 1

HCID 10813284HCID 10813284, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A 64 mg amount of N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-2,2-dimethyldodecaneamide (434) was dissolved in 0.5 ml of acetic anhydride, and 24 mg of nitric acid was slowly added to the solution while cooling the solution to 0° C. The mixture, as such, was allowed to react at 0° C. for one hour with stirring. The reaction solution was diluted with 5 ml of ice-cold water, 10 ml of a saturated aqueous sodium hydrogencarbonate solution was added thereto to effect neutralization, and the mixture was extracted with ethyl acetate (20 ml×twice). The organic layer was washed with water and brine in that order and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and 72 mg of the resultant crude product was purified by silica gel column chromatography (hexane/ethyl acetate) to provide 56 mg of the intended tittle compound. The yield was 78%.

Workup

  1. customto react at 0° C. for one hour
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (20 ml×twice)
  4. washThe organic layer was washed with water and brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation, and 72 mg of the resultant crude product
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68d71fad97a04b61aefcd0e50c5fca90
Source dataset
uspto-grants-1996_03
Patent number
US05496853

Reaction notes

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