Nitric Acid → 4-Chloro-3-nitropyridin-2-amine

HRID 1696197Notes

Reaction equation

HRID 1696197 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16]>O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[C:4]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 533020304-Chloropyridin-2-amine--hydrogen chloride (1/1)

Product 1

HCID 40716944-Chloro-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-2-pyridinamine hydrochloride (300 mg) was added portionwise to concentrated sulfuric acid (1.96 mL) at 4° C. To the mixture was added fuming nitric acid (0.1 mL) dropwise at 4° C. The mixture was stirred at ambient temperature for 3 hours. To the solution was added water and the mixture was extracted with EtOAc. The extract was washed with water, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc and n-hexane to give 4-chloro-3-nitro-2-pyridinamine (125 mg) as a yellow powder.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe extract was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with EtOAc and n-hexane

Sources & evidence

ORD record
ord-d038ee115cd04ba49517293d6c673ecc
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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