Nitric Acid → 1-Chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene

HRID 1059966Notes

Reaction equation

HRID 1059966 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:4]=1.[N+:16]([O-])([OH:18])=[O:17].C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=2)=[CH:10][C:11]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 186310154-(4-Methoxypyridin-2-yl)-chlorobenzene

Product 1

HCID 186675631-Chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 4-(4-methoxypyridin-2-yl)chlorobenzene (500 mg) in sulfuric acid (4 ml) was added fuming nitric acid (0.2 ml) dropwise at 0° C., and the mixture was stirred at 5° C. for 30 minutes. 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 triturated with diisopropyl ether, filtered, washed with diisopropyl ether and dried under reduced pressure to give 1-chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene (601 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 triturated with diisopropyl ether
  6. filtrationfiltered
  7. washwashed with diisopropyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-111a1b45b6f54895952c275907f26941
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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