Hydrochloric Acid → 2,4,5-Trichloropyridin-3-amine

HRID 2211006Notes

Reaction equation

HRID 2211006 reaction equation
OO.[NH2:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[Cl:10].C(=O)([O-])[O-].[Na+].[Na+].[ClH:18]>O>[NH2:3][C:4]1[C:5]([Cl:18])=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 10340Sodium CarbonateHCID 118508274,5-dichloropyridin-3-amine

Product 1

HCID 214644352,4,5-Trichloropyridin-3-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thirty percent aqueous hydrogen peroxide (3.0 g, 26 mmole) was added dropwise with stirring at 15° C. to a solution of 8.0 g (49 mmol) of 3-amino-4,5-dichloropyridine in 450 mL of 37 percent aqueous hydrochloric acid. After 30 min another 2.6 g (23 mmol) of 30 percent aqueous hydrogen peroxide was added and the solution was allowed to slowly warm to room temperature. The resulting mixture was diluted with water, neutralized with sodium carbonate, and extracted with ether. The ethereal extract was dried over magnesium sulfate and filtered. The filtrate was concentrated by evaporation under reduced pressure to obtain a viscous oil. This oil was partially purified by column chromatography to obtain 2.5 g (26 percent of theory) of the title compound, a white solid melting at 88°-90° C., and 5.3 g of a mixture of the title compound and 3-amino-2,4,5,6-tetrachloropyridine.

Workup

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  6. customto obtain a viscous oil
  7. customThis oil was partially purified by column chromatography

Sources & evidence

ORD record
ord-681c77f961254cb6a84506389ceed1cc
Source dataset
uspto-grants-1995_10
Patent number
US05461161

Reaction notes

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