Hydrochloric Acid → 2,4,6-Trichloro-3-nitropyridine

HRID 1190814Notes

Reaction equation

HRID 1190814 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](N)[CH:5]=[C:4]([Cl:12])[N:3]=1.[ClH:13].N([O-])=O.[Na+].[OH-].[Na+]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:13])[CH:5]=[C:4]([Cl:12])[N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2827402,6-Dichloro-3-nitropyridin-4-amineHCID 23668193Sodium Nitrite2×

Product 1

HCID 122757662,4,6-Trichloro-3-nitropyridineYield 80.7%

Conditions

Temperature
2.5 °C

Procedure

2,6-dichloro-3-nitropyridine-4-amine (2.27 g, 10.9 mmol) was added to 48 mL concentrated hydrochloric acid, and cooled to 0-5° C. To the solution was added sodium nitrite (2.26 g, 32.7 mmol) in batches. After the addition of sodium nitrite, the reaction solution was stirred for 1 h at 0-5° C., and then stirred for 2 h at 25° C., adjusted to pH=7 with 40% sodium hydroxide solution, and extracted with ethyl ether. After the organic phase was dried (Na2SO4) and concentrated, it was subjected to column chromatography eluted with petroleum ether to afford 2 g white solid with a yield of 80.7%.

Workup

  1. stirringstirred for 2 h at 25° C.
  2. extractionextracted with ethyl ether
  3. dry with materialAfter the organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. washeluted with petroleum ether

Sources & evidence

ORD record
ord-60852630ef314bbdb85be5cbac232f7d
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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