Aniline → alpha-(Phenylamino)benzeneacetic acid

HRID 1044032

Reaction equation

HRID 1044032 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].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:6]1([CH:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 19375alpha-(Phenylamino)benzeneacetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture was reacted in a closed vessel under microwave irradiation at 120° C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3×100 ml). The aqueous layer was acidified with 12N HCl (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield).

Workup

  1. customthe mixture was reacted in a closed vessel under microwave irradiation at 120° C. for 5 minutes (UPLC-MS monitoring: complete conversion)
  2. filtrationthe resulting solid was filtered
  3. addition2M Na2CO3 (50 ml) was added to the solution
  4. washthe aqueous layer was washed with DCM (3×100 ml)
  5. filtrationthe title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield)

Sources & evidence

ORD record
ord-f8037a5f69cc4c73b477b1e062b89c88
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Linked notes

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