Thionyl Chloride → 2,3-Dichloro-5-nitropyridine

HRID 1622079Notes

Reaction equation

HRID 1622079 reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.S(Cl)([Cl:14])=O>>[Cl:14][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178526838HCID 178526838, compound

Product 1

HCID 27631062,3-Dichloro-5-nitropyridine

Conditions

Temperature
100 °C

Procedure

3-Chloro-5-nitro-2-hydroxy-pyridine (20 g) was added in small portions to thionylchloride (200 mL) under vigorous stirring. The suspension was heated to 100° C. within 1 hour, stirred at 100° C. for 1 hour and then cooled to room temperature. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed with water (3×200 mL) and the organic layer was dried over MgSO4. The solvent was removed under reduced pressure to give 2,3-dichloro-5-nitropyridine (18 g) was obtained as a pale yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water (3×200 mL)
  5. dry with materialthe organic layer was dried over MgSO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c5c531f8bc034f2c9034bbb442c75aba
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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