HCID 53637388, compound → HCID 55285766, compound

HRID 2354066Notes

Reaction equation

HRID 2354066 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([CH3:12])[N+:4]=1[O-])[CH3:2]>CC(O)=O.[Fe]>[CH2:1]([C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([CH3:12])[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 53637388HCID 53637388, compound

Product 1

HCID 55285766HCID 55285766, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Ethyl-6-methyl-4-nitro-pyridine 1-oxide (27.65 g, 151.8 mmol) is dissolved in AcOH (330 mL) and Fe (powder, 33.9 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 (pH>10) with NaOH (1 M, 100 mL), filtered from the formed precipitate and the filtrate is extracted with CH2Cl2 (10×75 mL). The combined organic extracts are dried (MgSO4), filtered and evaporated 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 CH2Cl2 (10×75 mL)
  8. dry with materialThe combined organic extracts are dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-3795134896b44d5094be239780ffd047
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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