Nitric Acid → 2,6-DICHLORO-3-CHLOROMETHYL-5-NITROPYRIDINE

HRID 1283118Notes

Reaction equation

HRID 1283118 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][Cl:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([CH2:8][Cl:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[C:4]([Cl:10])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 6451791Pyridine, 2,6-dichloro-3-(chloromethyl)-

Product 1

HCID 122593812,6-DICHLORO-3-CHLOROMETHYL-5-NITROPYRIDINE

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
110 °C

Procedure

117.5 g (0.6 mol) of 2,6-dichloro-3-chloromethylpyridine are dissoled in a mixture of 540 ml of concentrated sulphuric acid and 600 ml of 100% strength fuming nitric acid. The reaction mixture is then heated at 110°C in an oil bath for 5 hours. After cooling to approx. 20°C, the reaction mixture is poured onto ice. The resulting crystals are filtered off and are purified by being well ground with water in a mortar and then filtered off with suction and rinsed with water on the filter. After drying the crude product in vacuo at 25°C over diphosphorus pentoxide. crude 2,6-dichloro-3-chloromethyl-5-nitropyridine is obtained in the form of pale yellow crystals, which can be recrystallised from methanol.

Workup

  1. temperatureAfter cooling to approx. 20°C
  2. additionthe reaction mixture is poured onto ice
  3. filtrationThe resulting crystals are filtered off
  4. customare purified
  5. filtrationfiltered off with suction
  6. washrinsed with water on the filter
  7. dry with materialAfter drying the crude product in vacuo at 25°C over diphosphorus pentoxide

Sources & evidence

ORD record
ord-e4a5895e955e4d60a58961997720b8c0
Source dataset
uspto-grants-1976_08
Patent number
US03974166

Reaction notes

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