Nitric Acid → HCID 18631021, compound

HRID 1059971Notes

Reaction equation

HRID 1059971 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17].C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 161260622-(4-Methoxyphenyl)-4-methylpyridine

Product 1

HCID 18631021HCID 18631021, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 4-(4-methylpyridin-2-yl)anisole (1.38 g) in sulfuric acid (3 ml) was added fuming nitric acid (0.5 ml) dropwise at 0° C., and the mixture was stirred at 5° C. for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The separated organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, 0-5% methanol in dichloromethane) to give 4-(4-methylpyridin-2-yl)-2-nitroanisole (378 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel 100 g, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8f3bbb3ab34f4a41ae9a844e45ae8d49
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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