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

HRID 76977

Reaction equation

HRID 76977 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].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 305145(4-Chloro-phenylamino)-phenyl-acetic acidYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of α-bromophenylacetic acid (1.00 g, 4.65 mmol) in acetonitrile (20 mL), is added 4-chloro-phenylamine (1.18 g, 9.30 mmol) and the mixture reacted in a closed vessel under MW irradiation at 100° C. for 1 hour (UPLC-MS monitoring: complete conversion). Solvent is evaporated and residue is portioned between EtOAc and 1N HCl. The organic phase is dried over Na2SO4, filtered and evaporated to dryness to get intermediate I76 as a yellow solid (0.57 g; 47% yield).

Workup

  1. customthe mixture reacted in a closed vessel under MW irradiation at 100° C. for 1 hour (UPLC-MS monitoring: complete conversion)
  2. customSolvent is evaporated
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto get intermediate I76 as a yellow solid (0.57 g; 47% yield)

Sources & evidence

ORD record
ord-00558b5248274d73b824daf6b95ba208
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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