Ethanol → HCID 58237096, compound

HRID 1188943Notes

Reaction equation

HRID 1188943 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH3:21])[CH:12]=2)=[CH:6][N:5]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH3:21][O:20][C:13]1[CH:12]=[C:11]([O:10][C:7]2[CH:6]=[N:5][C:4]([CH2:3][O:2][CH3:1])=[CH:9][CH:8]=2)[CH:16]=[CH:15][C:14]=1[NH2:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium Chloride2×HCID 58237106HCID 58237106, compound

Product 1

HCID 58237096HCID 58237096, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

A mixture of 2-(methoxymethyl)-5-(3-methoxy-4-nitrophenoxy)pyridine (27.0 g), iron (powder, 25.9 g), calcium chloride (1.03 g), ethanol (400 mL) and water (100 mL) was refluxed for 6 h. Then iron (powder, 12.9 g) and calcium chloride (1.03 g) were added to the mixture, and the whole was refluxed for further 2 h. The mixture was cooled to room temperature and filtered with celite. The filtrate was concentrated in vacuo to remove ethanol. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:3 to 3:1, volume ratio) to give the title compound (20.1 g, 83%) as a brown oil. MS 261 (MH+).

Workup

  1. temperaturewas refluxed for 6 h
  2. temperaturethe whole was refluxed for further 2 h
  3. filtrationfiltered with celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto remove ethanol
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:3 to 3:1, volume ratio)

Sources & evidence

ORD record
ord-1aa1ab0e9ca748159e8d2c55757e61a0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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