Ethanol → HCID 58237077, compound

HRID 1188902Notes

Reaction equation

HRID 1188902 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O)[O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:23]=[CH:24][C:25]=1[NH2:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 58237034HCID 58237034, compound

Product 1

HCID 58237077HCID 58237077, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-[3-(benzyloxy)-4-nitrophenoxy]-2-(methylsulfonyl)pyridine (28.0 g), calcium chloride (0.78 g), iron (powder, 19.0 g), ethanol (500 mL) and water (110 mL) was refluxed for 5 h. The mixture was cooled to 40° C. and filtered through a celite pad. The filtrate was concentrated in vacuo to remove ethanol. The residue was partitioned between ethyl acetate and brine. 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=2:1, volume ratio) to give the title compound (26.0 g, 100%) as light brown crystals. MS 371 (MH+).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto remove ethanol
  5. customThe residue was partitioned between ethyl acetate and brine
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1, volume ratio)

Sources & evidence

ORD record
ord-0a64a293616a47e8a9f28e2097493451
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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