2-Chloro-5-nitropyridine → HCID 4418042, compound

HRID 1033197Notes

Reaction equation

HRID 1033197 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1>C(NCC)C.C(Cl)Cl>[CH2:2]([N:3]([CH2:4][CH3:5])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH3:7]

Participants

4

Reactant 1

HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 4418042HCID 4418042, compoundYield 195.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

A stirred mixture of 27.6 g (0.174 mole) of 2-chloro-5-nitropyridine in 500 ml of diethylamine was heated at reflux for two days. The excess diethylamine was removed by distillation under reduced pressure, leaving a residue. This residue was dissolved in methylene chloride, and the organic solution was washed with an aqueous, 10% sodium hydroxide solution. The washed organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure to yield 33.2 g of 2-diethylamino-5-nitropyridine as a solid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. customThe excess diethylamine was removed by distillation under reduced pressure
  4. customleaving a residue
  5. washthe organic solution was washed with an aqueous, 10% sodium hydroxide solution
  6. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  7. filtrationwas filtered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1cf74df28d19415a9555a9df54a325cc
Source dataset
uspto-grants-1994_05
Patent number
US05310724

Reaction notes

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