2-Chloro-3-nitropyridine → HCID 13911193, compound

HRID 979407Notes

Reaction equation

HRID 979407 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Na].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1>CN(C=O)C>[N+:8]([C:7]1[C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 13911193HCID 13911193, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 10 g of 2-chloro-3-nitropyridine dissolved in 30 ml of dry DMF was added dropwise to a suspension containing 6.9 g of 1,2,4-triazole sodium salt (90%, Aldrich Chemical Co.) in 40 ml of dry DMF. After a slow exotherm had subsided, the suspension was heated at 60° for three hours then cooled to 25° C. and poured onto 500 ml of ice-water to yield a precipitate. After the mixture was filtered, the isolated solid was washed 2×50 ml of water and suction-dried to yield 12 g of crude product. The product was recrystallized from 2-propanol to yield 8 g of the subject compound; m.p. 131°-133°.

Workup

  1. additionwas added dropwise to a suspension
  2. temperaturethe suspension was heated at 60° for three hours
  3. customto yield a precipitate
  4. filtrationAfter the mixture was filtered
  5. washthe isolated solid was washed 2×50 ml of water
  6. customsuction-dried
  7. customto yield 12 g of crude product
  8. customThe product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-332768f1637b47c49d526f2d6447d2fa
Source dataset
uspto-grants-1987_05
Patent number
US04668279

Reaction notes

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