Ammonium Chloride → HCID 53694082, compound

HRID 1276223Notes

Reaction equation

HRID 1276223 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[Cl:19])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=1[Cl:19])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 53664753HCID 53664753, compound

Product 1

HCID 53694082HCID 53694082, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (4-nitro-2,6-dichloro-phenoxy)-acetic acid tert-butyl ester (1 g) in ethanol (17 mL) and water (8.6 mL) is treated with iron powder (0.861 g) and ammonium chloride (86 mg) and the mixture is heated to reflux for approximately 1 hour. The mixture is then filtered and concentrated under reduced pressure. The resulting oil is partitioned between water and ethyl acetate, and the organic phase is then washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide the desired compound as a pale yellow solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for approximately 1 hour
  3. filtrationThe mixture is then filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil is partitioned between water and ethyl acetate
  6. washthe organic phase is then washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85d57945213147d09e3f9acb1506e636
Source dataset
uspto-grants-2000_12
Patent number
US06166028

Reaction notes

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