2,4,6-Trimethyl-3-nitropyridine → 2,4,6-Trimethyl-3-pyridinamine

HRID 1872064Notes

Reaction equation

HRID 1872064 reaction equation
[N+:1]([C:4]1[C:5]([CH3:12])=[N:6][C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([CH3:12])=[N:6][C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 1

HCID 27476982,4,6-Trimethyl-3-nitropyridine

Product 1

HCID 988462,4,6-Trimethyl-3-pyridinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Nitro-2,4,6-trimethylpyridine (14.89 g, 89.70 mmol) in methanol (250 ml) containing 10% palladium/carbon (1.5 g) was hydrogenated at 55 psi for 2 hours. The reaction mixture was filtered through wet celite, and the celite filter rinsed with methanol (5×30 ml). The filtrate was concentrated in vacuo to dryness and the residue purified by chromatography (silica gel; methylene chloride/methanol, 95/5) to 3-amino-2,4,6-trimethylpyridine (12.42 g, 100%) as a viscous oil.

Workup

  1. filtrationThe reaction mixture was filtered through wet celite
  2. filtrationthe celite filter
  3. washrinsed with methanol (5×30 ml)
  4. concentrationThe filtrate was concentrated in vacuo to dryness
  5. customthe residue purified by chromatography (silica gel; methylene chloride/methanol, 95/5) to 3-amino-2,4,6-trimethylpyridine (12.42 g, 100%) as a viscous oil

Sources & evidence

ORD record
ord-3198ed2322d8423180688cdb50cfae3e
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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