Thionyl Chloride → 2-Chloro-5-methyl-3-nitropyridine

HRID 2210429Notes

Reaction equation

HRID 2210429 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178430719HCID 178430719, compound

Product 1

HCID 8183002-Chloro-5-methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of 2-hydroxy-5-methyl-3-nitropyridine are dissolved in 32 cm3 of thionyl chloride to which 2 cm3 of N,N-dimethylformamide have been added. The mixture is then brought to reflux for 2 hours. After removing the solvent under partial vacuum, the product is distributed between distilled water (30 cm3) and chloroform (3×100 cm3). The chloroform fractions are combined, dried over MgSO4, filtered and then concentrated under vacuum. The residue is recrystallized from ethanol/water. Yd.: 60-65%

Workup

  1. additionhave been added
  2. temperatureto reflux for 2 hours
  3. customAfter removing the solvent under partial vacuum
  4. distillationbetween distilled water (30 cm3) and chloroform (3×100 cm3)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue is recrystallized from ethanol/water

Sources & evidence

ORD record
ord-4384efdf0304405790587a70c99f4424
Source dataset
uspto-grants-1995_10
Patent number
US05459138

Reaction notes

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