Aniline → 2-Anilinophenylacetic acid

HRID 277205Notes

Reaction equation

HRID 277205 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN1CCCC1=O>[C:13]1([NH:12][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 877542-Bromophenylacetic acid

Product 1

HCID 8540572-Anilinophenylacetic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-bromophenylacetic acid (25 mmol) was added to a mixture of 50 mmol of aniline, 50 mmol of anhydrous potassium carbonate, (7%) mmol of activated copper powder, and 3 ml of N-methylpyrrolidone at 120° C. The mixture was kept at 120° C. for 4 h with stirring. The resulting slightly grayish mixture was filtered while hot through a bed of Celite and the Celite was washed with water (200 ml) and hexane (200 ml). The filtrate was transferred to a separating funnel and extracted with hexane and cooled to room temperature. The aqueous layer was removed, cooled to 5° C., and neutralized with dilute hydrochloric acid (1:3) which was also kept at 5° C. The precipitated 2-[(phenyl)amino]phenylacetic acid was collected by filtration, thoroughly washed with water, and dried under suction.

Workup

  1. filtrationThe resulting slightly grayish mixture was filtered while hot through a bed of Celite
  2. washthe Celite was washed with water (200 ml) and hexane (200 ml)
  3. customThe filtrate was transferred to a separating funnel
  4. extractionextracted with hexane
  5. customThe aqueous layer was removed
  6. temperaturecooled to 5° C.
  7. customwas also kept at 5° C
  8. filtrationThe precipitated 2-[(phenyl)amino]phenylacetic acid was collected by filtration
  9. washthoroughly washed with water
  10. customdried under suction

Sources & evidence

ORD record
ord-6e150abcf00840849a02ec68579023f1
Source dataset
uspto-grants-2002_03
Patent number
US06355680B1

Reaction notes

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