Nitric Acid → 2-Amino-4,6-dimethyl-3-nitropyridine

HRID 1457785Notes

Reaction equation

HRID 1457785 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 215072-Amino-4,6-dimethylpyridine

Product 1

HCID 2984722-Amino-4,6-dimethyl-3-nitropyridineYield 52%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

6.0 g(0.04911 mole) of 2-amino-4,6-dimethyl pyridine was dissolved in 20 ml of conc. sulfuric acid. The reaction solution was cooled to 0° C. in an ice bath and thereto was added dropwise 2.3 ml(0.04911 mole) of conc. nitric acid diluted with 5 ml of conc. sulfuric acid over 10 minutes. The resultant was stirred for 30 minutes at 0° C. and then added into ice water slowly to terminate the reaction. The reaction solution was neutralized to pH 7-8 with 20% aqueous sodium hydroxide solution and extracted with ethyl acetate(100 ml×3). The organic layer was dried over sodium sulfate anhydride and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to obtain 4.26 g of the title compound as a yellow solid(yield 52%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionextracted with ethyl acetate(100 ml×3)
  4. dry with materialThe organic layer was dried over sodium sulfate anhydride
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-a584d1c83c394006a2b2582449985bf6
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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