Ethanol → HCID 69521789, compound

HRID 856713Notes

Reaction equation

HRID 856713 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12]N=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[Ca+2].[Cl-].[CH2:22](O)C>>[CH3:1][C:2]1[C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:22]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 69522179HCID 69522179, compound

Product 1

HCID 69521789HCID 69521789, compound

Procedure

To 2-methyl-3-[[(5-nitro-2-pyridinyl)sulfanyl]methyl]pyridine (4.0 g) was added 85% aqueous solution of ethanol (80 ml), calcium chloride (0.86 g) and reduced iron (4.3 g) were added to the mixture, and the mixture was heated to reflux for 3 hours. After allowing the mixture to be cooled to room temperature, and the solvent was removed under reduced pressure. The mixture was filtered with. Celite, and washed with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[(2-methyl-3-pyridinyl)methyl]sulfanyl]aniline (3.2 g).

Workup

  1. additionwere added to the mixture
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. customthe solvent was removed under reduced pressure
  5. filtrationThe mixture was filtered with
  6. washCelite, and washed with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8ea0477ba48c43969d474dad51dace98
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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