5-Tert-butyl-2-methyl-3-nitro-pyridine → 5-Tert-butyl-2-methyl-pyridin-3-ylamine

HRID 735797Notes

Reaction equation

HRID 735797 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[C:8]([CH3:11])=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([NH2:12])[C:8]([CH3:11])=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 210243025-Tert-butyl-2-methyl-3-nitro-pyridine

Product 1

HCID 210243035-Tert-butyl-2-methyl-pyridin-3-ylamineYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above pyridine (388 mg, 1.99 mmol) was dissolved in ethanol (6 mL) and placed in a Parr hydrogenation vessel. Pd (10% on carbon, 20 mg) was added and the reaction was placed under a hydrogen atmosphere (50 psi) and shaken at room temperature for 18 h. The solution was then filtered through diatomaceous earth, concentrated in vacuo to provide 5-tert-butyl-2-methyl-pyridin-3-ylamine (340 mg, 99%) as a pale orange solid: ESI MS m/z 164 [C10H16N2+H]+.

Workup

  1. filtrationThe solution was then filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6f6170e0f10472d8e51401a2e961215
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

Loading…