2,6-Lutidine, 4-nitro-, 1-oxide → 4-Amino-2,6-dimethylpyridine

HRID 2354059Notes

Reaction equation

HRID 2354059 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-]>CC(O)=O.[Fe]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

4

Reactant 1

HCID 209452,6-Lutidine, 4-nitro-, 1-oxide

Product 1

HCID 770474-Amino-2,6-dimethylpyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2,6-Dimethyl-4-nitro-pyridine 1-oxide (9.62 g, 57 mmol) is dissolved in AcOH (300 mL) and Fe (powder, 29 g) is added. The mixture is stirred for 1 h at 100° C. The mixture is cooled to r.t. and filtered. The filtercake is thoroughly washed with AcOH and then discarded. The filtrate is evaporated, diluted with water (100 mL), basified with NaOH (1 M, 100 mL), filtered from the formed precipitate and the filtrate is extracted with CHCl3 (10×50 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated. The residue is crystallized from heptane-CHCl3 to provide the title compound.

Workup

  1. temperatureThe mixture is cooled to r.t.
  2. filtrationfiltered
  3. washThe filtercake is thoroughly washed with AcOH
  4. customThe filtrate is evaporated
  5. additiondiluted with water (100 mL)
  6. filtrationfiltered from the formed precipitate
  7. extractionthe filtrate is extracted with CHCl3 (10×50 mL)
  8. dry with materialThe combined organic extracts are dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized from heptane-CHCl3

Sources & evidence

ORD record
ord-6d10d6d1c5cb4708b04dcc62c036f6fb
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

Loading…