Hydrochloric Acid → HCID 43259353, compound

HRID 1393080Notes

Reaction equation

HRID 1393080 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[F:16])[CH3:2].Cl>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[F:16])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 43259205HCID 43259205, compound

Product 1

HCID 43259353HCID 43259353, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2-fluoro-4-nitro-phenoxy)-acetic acid ethyl ester (17.0 g, 55.92 mmol) in EtOH (330 ml) and aqueous 1M HCl (55.92 ml, 55.92 mmol) was hydrogenated in the presence of 10% Pd/C (1.7 g) for 2 days. After removal of the catalyst the reaction was evaporated and treated with water/Et2O (3×), the aqueous phase was treated with NaHCO3 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 5.39 g (45%) of (4-amino-2-fluoro-phenoxy)-acetic acid ethyl ester as a brown crystallin residue, MS: 213 (M+).

Workup

  1. customAfter removal of the catalyst the reaction
  2. customwas evaporated
  3. additiontreated with water/Et2O (3×)
  4. additionthe aqueous phase was treated with NaHCO3
  5. extractionextracted with Et2O (3×)
  6. washThe organic phases were washed with aqueous 10% NaCl
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-8ae497ecb8e8456a9da5e19ce448c878
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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