Ethanol → HCID 67118502, compound

HRID 1188899Notes

Reaction equation

HRID 1188899 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][N:10]=1)[CH3:3].[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:11][N:10]=2)[CH:19]=[CH:20][C:21]=1[NH2:22])[CH3:1]

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 66885609HCID 66885609, compound

Product 1

HCID 67118502HCID 67118502, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-(1-methylethoxy)-4-nitrophenoxy]-5-(methylsulfonyl)pyridine (39.89 g), iron powder (31 g), calcium chloride (1.3 g), ethanol (400 mL) and water (100 mL) was stirred at 80° C. for 3 h. The mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Water and brine were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether-hexane to give the title compound (32 g, 88%) as a brownish solid. MS 323 (MH+).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater and brine were added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residual solid was washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-02df000acb3f4c4ca4a1bead359badd5
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…