Nitric Acid → 2,3,6-Trichloro-5-nitropyridine

HRID 1283117Notes

Reaction equation

HRID 1283117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>>[Cl:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[N:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 230162,3,6-Trichloropyridine

Product 1

HCID 122593792,3,6-Trichloro-5-nitropyridineYield 66.7%

Conditions

Temperature
100 °C

Procedure

3.6 g. (0.02 mol) of 2,5,6-trichloropyridine are dissolved in a mixture of 20 ml of 100% strength fuming nitric acid and 16 ml of concentrated sulphuric acid and are then heated at 100°C in an oil bath for 12 hours. After cooling to approx. 20°C, the reaction mixture is poured onto ice. The crude product is produced in the form of slightly yellowish crystals, which are filtered off with suction, washed with water and dried at 30°C in vacuo over KOH. 3 g (66.7% of theory) of 2,5,6-trichloro-3-nitropyridine are obtained in the form of crystals which, after sublimation at 30° - 40°C/12 mm Hg. melt at 68° - 70°C.

Workup

  1. temperatureAfter cooling to approx. 20°C
  2. additionthe reaction mixture is poured onto ice
  3. customThe crude product is produced in the form of slightly yellowish crystals, which
  4. filtrationare filtered off with suction
  5. washwashed with water
  6. dry with materialdried at 30°C in vacuo over KOH

Sources & evidence

ORD record
ord-598b895c6bc942adbfd554c7b061a785
Source dataset
uspto-grants-1976_08
Patent number
US03974166

Reaction notes

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