Water → HCID 58158590, compound

HRID 2095763Notes

Reaction equation

HRID 2095763 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][C:3]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:2]([F:1])[CH:7]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 58158630HCID 58158630, compound

Product 1

HCID 58158590HCID 58158590, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzyl {2-fluoro-4-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (40 g, 104.3 mmol) in ethanol (1020 mL)/water (180 mL) were added reduced iron (29.1 g, 521.7 mmol) and calcium chloride (5.8 g, 52.2 mmol), and the mixture was heated under reflux for 8 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with ethanol. The solvent was evaporated under reduced pressure, water (200 mL) was added to the residue, and the mixture was extracted with ethyl acetate (800 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, hexane/ethyl acetate (=3/1) was added, and the precipitate was collected by filtration to give the title compound (28.2 g, 76%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. filtrationfiltered through celite
  4. washwashed with ethanol
  5. customThe solvent was evaporated under reduced pressure, water (200 mL)
  6. additionwas added to the residue
  7. extractionthe mixture was extracted with ethyl acetate (800 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, hexane/ethyl acetate (=3/1)
  11. additionwas added
  12. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5171d3c7fddc45af8bbe3293270cf85c
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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