Sodium Hydroxide → 4-(2-((4-Methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoic acid

HRID 923596Notes

Reaction equation

HRID 923596 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[C:5]([C:23]([F:26])([F:25])[F:24])[CH:4]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[C:5]([C:23]([F:24])([F:26])[F:25])[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71076800Methyl 4-(2-((4-methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoate

Product 1

HCID 710769264-(2-((4-Methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Prepared using General Procedure 9: To a stirring solution of methyl 4-(2-((4-methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoate INT-54 (113 mg, 0.31 mmol) in EtOH (10 mL) was added 1 N NaOH (1 mL). The reaction mixture was heated to 50° C. for 3 h, concentrated, diluted with water, acidified with 1 N HCl and extracted with EA and DCM. The organic layers were combined, dried over Na2SO4 and concentrated to provide 97 mg (89%) of 4-(2-((4-methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoic acid INT-55. LCMS-ESI (m/z) calculated for C17H14F3NO4: 353; found 354 [M+H]+, tR=2.84 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 8.13 (d, J=8.2 Hz, 2H), 8.04 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H), 7.13 (s, 1H), 7.05 (m, 2H), 3.82 (m, 5H).

Workup

  1. customPrepared
  2. concentrationconcentrated
  3. additiondiluted with water
  4. extractionextracted with EA and DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0474216d80c343938ee7a9d096315e97
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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