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

HRID 1255088Notes

Reaction equation

HRID 1255088 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-ffd0898249004bcca62db00dd2bf8a91
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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