2-Amino-6-methyl-3-nitropyridine → 6-Methylpyridine-2,3-diamine

HRID 642865Notes

Reaction equation

HRID 642865 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][CH:3]=1>CO>[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 2260282-Amino-6-methyl-3-nitropyridine

Product 1

HCID 27344206-Methylpyridine-2,3-diamineYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Methyl-3-nitro-pyridin-2-ylamine (1.3 g, 8.5 mmol) was dissolved in methanol (40 ml). The flask was purged of all oxygen, placed under a nitrogen atmosphere, and charged with Pd/C (150 mg of 10% palladium on carbon). The reaction mixture was purged, and placed under a hydrogen atmosphere, maintained with a balloon. It was allowed to stir for 18 h until the reduction was judged complete. It was then filtered through Celite™ to remove the palladium. The solvent was removed under vacuum to yield the title compound (1.01 g, 96%). 1H NMR (DMSO-d6): δ=6.59 (d, 1H, J=7.5 Hz), 6.19 (d, 1H, J=7.5 Hz), 5.23 (bs, 2H), 4.39 (bs, 2H), 2.11 (s, 3H).

Workup

  1. customThe flask was purged of all oxygen
  2. additioncharged with Pd/C (150 mg of 10% palladium on carbon)
  3. customThe reaction mixture was purged
  4. temperaturemaintained with a balloon
  5. filtrationIt was then filtered through Celite™
  6. customto remove the palladium
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3d4f1e8890094c83b6291422c1739e3b
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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