Water → HCID 58158506, compound

HRID 2095752Notes

Reaction equation

HRID 2095752 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 58158492HCID 58158492, compound

Product 1

HCID 58158506HCID 58158506, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzyl {4-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (5.99 g, 16.4 mmol) in ethanol (80 mL)/water (16 mL) were added reduced iron (5.8 g, 98.4 mmol) and calcium chloride (1.42 g, 11.5 mmol), and the mixture was heated under reflux for 16 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with ethanol. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate (50 mL) was added to the residue, and the mixture was extracted with ethyl acetate (150 mL). The organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, a solid was precipitated with hexane/ethyl acetate (=2/1, 30 mL) and collected by filtration to give the title compound (4.43 g, 81%). The solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (NH silica, hexane/ethyl acetate=3/1→1/3) to give the title compound (0.43 mg, 8%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hr
  3. filtrationfiltered through celite
  4. washwashed with ethanol
  5. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate (50 mL)
  6. additionwas added to the residue
  7. extractionthe mixture was extracted with ethyl acetate (150 mL)
  8. washThe organic layer was washed with water and saturated brine in this order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customa solid was precipitated with hexane/ethyl acetate (=2/1, 30 mL)
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9f20f1e20eff412f9bc0991adb90d104
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

Loading…