Acetic Acid → HCID 57667927, compound

HRID 2191677Notes

Reaction equation

HRID 2191677 reaction equation
O.NN.[CH2:4]([N:11]([C:15]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])C(=O)C)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C.[Cl-].[Na+]>C(OCC)(=O)C>[CH2:4]([NH:11][C:15]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 57667917HCID 57667917, compound

Product 1

HCID 57667927HCID 57667927, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of hydrazine monohydrate 2.0 mL of 2-(N-benzylacetamido)-4-phenoxybenzoic acid 0.10 g was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, acetic acid 5.0 mL was added to it, and ethyl acetate and saturated sodium chloride aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate:acetic acid=80:20:1] to give 2-(benzylamino)-4-phenoxybenzoic acid 20 mg of white solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 3 hours
  3. additionwere added to it
  4. customThe organic layer was separated
  5. customcollected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df6ed5e3841341e59dec72a809775e64
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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