2-Aminopyridine → 3,5-Dinitropyridine

HRID 1974017Notes

Reaction equation

HRID 1974017 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.C(=O)(O)[O-].[K+].NC1C=CC=CN=1>>[N+:11]([C:5]1[CH:4]=[N:3][CH:2]=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1)([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 104392-AminopyridineHCID 757382-Chloro-3,5-dinitropyridineHCID 516893Potassium Bicarbonate

Product 1

HCID 5980543,5-DinitropyridineYield 81%

Procedure

A mixture of 2-chloro-3,5-dinitropyridine (20.4 g, 0.10 mole) 15 ml absolute ethanol, potassium bicarbonate (11.0 g, 0.11 mole), and 2-aminopyridine (28.2 g, 0.30 mole) was refluxed for 24 hours. The mixture was concentrated to one-half of its volume and diluted with several volumes of water to precipitate solid. After further washing and drying 2-α-pyridylamino)-3,5-dinitropyridine (81% yield) was obtained as a golden, yellow solid. Anal. Calcd. for C10H7N5O4 : C, 46.0; H, 2.7; N, 26.8 Found: C, 46.1; H, 2.9; N, 27.0.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe mixture was concentrated to one-half of its volume
  3. additiondiluted with several volumes of water
  4. customto precipitate solid
  5. washAfter further washing

Sources & evidence

ORD record
ord-399cfc1d2f6541cca592e415ecba7bb0
Source dataset
uspto-grants-1976_12
Patent number
US04000146

Reaction notes

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