Acetic Acid → HCID 57667856, compound

HRID 2191630Notes

Reaction equation

HRID 2191630 reaction equation
O.NN.C([NH:7][C:8]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])(=O)C.C(O)(=O)C.[Cl-].[Na+]>C(OCC)(=O)C>[NH2:7][C:8]1[CH:16]=[C:15]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 57667800HCID 57667800, compound

Product 1

HCID 57667856HCID 57667856, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of hydrazine monohydrate 5.0 mL of 2-(acetamido)-4-phenoxybenzoic acid 1.5 g was heated and refluxed for 4 hours. After the reaction mixture was cooled to room temperature, acetic acid 10 mL, ethyl acetate and saturated sodium chloride aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue, solid matter was filtrated to give 2-amino-4-phenoxybenzoic acid 1.2 g of white solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 4 hours
  3. customThe organic layer was separated
  4. customthe solvent was removed under reduced pressure
  5. additionDiisopropyl ether and hexane were added to the obtained residue, solid matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-f7df852aa812407888497df0cefaa2d1
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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