3-Methoxyaniline → (3-Methoxy-phenylamino)-phenyl-acetic acid

HRID 76998Notes

Reaction equation

HRID 76998 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:17][CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 2759625(3-Methoxy-phenylamino)-phenyl-acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-2-phenylacetic acid (0.5 g, 2.28 mmol) and 3-methoxyaniline (0.54 mL, 4.56 mmol) in THF (12 mL) is refluxed for 4 hours. Solvent is removed under vacuum, the residue is taken up with 1M HCl and extracted with EtOAc. The organic phase is dried (Na2SO4), filtered and evaporated. The crude is purified by flash chromatography (DCM/MeOH=98/2 to 9/1) to obtain intermeaditae I116 as a white solid (0.58 g, 99% yield).

Workup

  1. customSolvent is removed under vacuum
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude is purified by flash chromatography (DCM/MeOH=98/2 to 9/1)

Sources & evidence

ORD record
ord-d2075340269f4f199e1ba8a3ca303395
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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