Nitric Acid → HCID 86720742, compound

HRID 2167686Notes

Reaction equation

HRID 2167686 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[N+:12]([O-])([OH:14])=[O:13]>O>[CH3:1][C:2]1[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27753Acetonitrile, (2,5-xylyl)-

Product 1

HCID 86720742HCID 86720742, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To (2,5-dimethylphenyl)acetonitrile (30 g), under ice cooling, fuming nitric acid (103 mL) was added dropwise, and the resultant was stirred for 30 minutes under ice cooling. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH-type silica gel; chloroform/ethyl acetate-gradient elution=100/0→90/10) and then further purified twice by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→60/40) to obtain the title compound (12 g) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationthe desiccant was filtered off
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. additionA saturated aqueous solution of sodium bicarbonate was added to the obtained residue
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationthe desiccant was filtered off
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (NH-type silica gel; chloroform/ethyl acetate-gradient elution=100/0→90/10)
  11. customfurther purified twice by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→60/40)

Sources & evidence

ORD record
ord-064ee7097b6847aa825ccdd6723ce924
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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