2-Fluoroaniline → 4-(((2-Fluorophenyl)amino)methyl)benzoic acid

HRID 1968443Notes

Reaction equation

HRID 1968443 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].[B][B][B][B][B][B][B][B][B][B]>CO>[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][CH2:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 120884-Formylbenzoic acidHCID 178419135HCID 178419135, compound

Product 1

HCID 393485394-(((2-Fluorophenyl)amino)methyl)benzoic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-formylbenzoic acid 47a (3.33 mmol, 500 mg), 2-fluoroaniline 47b (3.33 mmol, 370 mg), and decaborane (1 mmol, 122 mg) in 8 mL of MeOH was stirred at room temperature for 15 min. The mixture was concentrated and purified by preparative reverse-phase chromatography to afford 0.81 g (99%) of 47c.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative reverse-phase chromatography

Sources & evidence

ORD record
ord-2bcbd73be788460ea2164bdf3b41e913
Source dataset
uspto-grants-2013_04
Patent number
US08426401B2

Reaction notes

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