Aniline → (4-Chloro-phenyl)-phenylamino-acetic acid

HRID 77055Notes

Reaction equation

HRID 77055 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 10490868alpha-Bromo-4-chlorophenylacetic acid

Product 1

HCID 2757838(4-Chloro-phenyl)-phenylamino-acetic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-2-(4-chlorophenyl)acetic acid (1.2 g, 4.67 mmol) and aniline (0.85 mL, 9.33 mmol) are dissolved in acetonitrile (29 mL). The reaction is heated under microwave irradiation at 100° C. for 5 minutes. The solvent is evaporated and the residue is dissolved in EtOAc and washed with 3M HCl and then brine. The organic layer is dried over Na2SO4, filtered and evaporated to dryness to give intermediate I258 as a white solid (1.22 g, quantitative yield).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with 3M HCl
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b5b9b1b80fe0497e81a29222e9861894
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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