Nitric Acid → 2-Amino-6-methyl-3-nitropyridine

HRID 1601082Notes

Reaction equation

HRID 1601082 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[N+:9]([O-])([OH:11])=[O:10].[OH-].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridine

Product 1

HCID 2260282-Amino-6-methyl-3-nitropyridineYield 24%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-30 °C

Procedure

2-Amino-6-picoline (5.1 g, 47.1 mmol) was weighed into a 500 mL round bottom flask, and the flask was cooled to -30° C. Concentrated H2SO4 (20 mL) was added, which caused some fuiming to occur. Concentrated HNO3 (10 mL, 160 mmol) was then added dropwise slowly. The reaction was allowed to warm to RT over 30 min, then was heated in an oil bath set at 80° C. After 90 min, the reaction was removed from the heating bath, and ice was added. 6.25 N NaOH (150 mL, 937.5 mmol) was added slowly, and the resulting yellow precipitate was collected on a sintered glass funnel. Drying in a vacuum desiccator gave the title compound (1.7 g, 24%): TLC Rf (5% MeOH/CHCl3) 0.77; 1H NMR (250 MHz, CDCl3) δ 8.31 (d, 1H), 6.32 (d, 1H), 2.46 (s, 3H); MS (ES) m/e 154.0 (M+H)+.

Workup

  1. temperatureto warm to RT over 30 min
  2. temperaturewas heated in an oil bath
  3. customset at 80° C
  4. customthe reaction was removed from the heating bath, and ice
  5. additionwas added
  6. customthe resulting yellow precipitate was collected on a sintered glass funnel
  7. customDrying in a vacuum desiccator

Sources & evidence

ORD record
ord-ad6e38f687fc4572805d844a2918a5e9
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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