Ammonium Chloride → HCID 67040794, compound

HRID 605353Notes

Reaction equation

HRID 605353 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:13][CH:12]=2)=[C:6]([N+:25]([O-])=O)[CH:5]=1.[NH4+].[Cl-]>CCO.O(C(C)C)C(C)C.[Fe]>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:15][CH:16]=2)=[C:6]([NH2:25])[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67040780HCID 67040780, compound

Product 1

HCID 67040794HCID 67040794, compoundYield 63.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A suspension of 4-(4-tert-butoxycarbonylamino-phenoxy)-3-nitro-benzoic acid methyl ester (18.0 g, 46 mmol), Fe powder (13.5 g, 232 mmol) and NH4Cl (12.4 g, 232 mmol) in aqueous EtOH [prepared from EtOH (180 mL) and H2O (180 mL)] was gradually heated to reflux and refluxed for 1.5 hours. The reaction mixture was filtrated through celite pad and the filtrate was evaporated. The aqueous residue was portioned between AcOEt and 5% NaHCO3 and then filtered through celite pad. The organic layer was separated, washed H2O and brine, dried over MgSO4 and evaporated to give pale brown oil, which was diluted with i-Pr2O (100 mL) and stirred at room temperature for 1 hour. The resulting crystal was collected by filtration, washed with i-Pr2O, and dried at 40° C. overnight under reduced pressure to give the title compound as colorless crystal (10.5 g, 63%).

Workup

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. temperaturerefluxed for 1.5 hours
  4. filtrationThe reaction mixture was filtrated through celite pad
  5. customthe filtrate was evaporated
  6. filtrationfiltered through celite pad
  7. customThe organic layer was separated
  8. washwashed H2O and brine
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customto give pale brown oil, which
  12. filtrationThe resulting crystal was collected by filtration
  13. washwashed with i-Pr2O
  14. customdried at 40° C. overnight under reduced pressure

Sources & evidence

ORD record
ord-24a1061c5b7c46adae0f99f9b26e0763
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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