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

HRID 642864

Reaction equation

HRID 642864 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[N+:9]([O-])([OH:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>OS(O)(=O)=O>[CH3:8][C:6]1[N:7]=[C:2]([NH2:1])[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 10340Sodium CarbonateHCID 157652-Amino-6-methylpyridine

Product 1

HCID 2260282-Amino-6-methyl-3-nitropyridineYield 19%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6-Amino picoline (5.0 g, 46 mmol) was cautiously suspended in H2SO4 (25 ml) and cooled in an ice bath. Fuming nitric acid (5 ml) was added slowly, and care was taken to keep the temperature of the reaction as low as possible. The reaction mixture was allowed to stir 3 h after the addition of the nitric acid was complete. The mixture was added to sodium carbonate (65 g), suspended in about ice water (500 ml). Once the neutralization was complete, the aqueous mixture was extracted four times with ethyl acetate. The combined ethyl acetate washings were washed with brine, dried using MgSO4, and concentrated under vacuum to yield the title product (1.3 g, 19%) as a red oil. 1H NMR (DMSO-d6): δ=8.27 (d, 1H, J=8.5 Hz), 7.88 (bs, 2H), 6.63 (1H, d, J=8.5), 2.39 (s, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. customthe temperature of the reaction as low as possible
  3. extractionthe aqueous mixture was extracted four times with ethyl acetate
  4. washThe combined ethyl acetate washings were washed with brine
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-66fb8469d6ec44f885c091c3febe586a
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Linked notes

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