Acetonitrile → 4-Methyl-phenyl-amino-phenyl-acetic acid

HRID 77047

Reaction equation

HRID 77047 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].[CH3:12][C:13]1[CH:18]=[CH:17][C:16](N)=[CH:15][CH:14]=1.C(#[N:22])C>>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]([NH2:22])([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 3

HCID 6342AcetonitrileHCID 7813p-ToluidineHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 2378904-Methyl-phenyl-amino-phenyl-acetic acidYield 78%

Procedure

To a solution of α-bromophenylacetic acid (1.00 g, 4.65 mmol) in acetonitrile (20 mL), is added 4-methyl-phenylamine (0.96 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 2N HCl. The organic phase is dried over Na2SO4, filtered and evaporated to dryness to get desired compound as a yellow solid (0.88 g, 78% 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

Sources & evidence

ORD record
ord-78136e439632492782ede2e4ddd841ae
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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