Methanol → 4-[(3,4-Dimethoxyphenylamino)-methyl]-benzoic Acid

HRID 252801Notes

Reaction equation

HRID 252801 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)=O.C1([SiH3])C=CC=CC=1.CO>COCCOC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH2:12][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 887MethanolHCID 120884-Formylbenzoic acidHCID 12752PhenylsilaneHCID 227703,4-Dimethoxyaniline

Product 1

HCID 224788804-[(3,4-Dimethoxyphenylamino)-methyl]-benzoic AcidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3,4-dimethoxy-phenylamine (786 mg; 5.13 mmol) and dibutyltridichloride (219 mg; 0.72 mmol) in ethyleneglycol dimethylether (7 mL), 4-formyl-benzoic acid (748 mg; 4.98 mmol) was added. The suspension was stirred at room temperature for 10 min, treated with phenylsilane (1.0 mL; 7.9 mmol) and the mixture stirred at the same temperature for 12 h. Methanol and a few drops of water were added, stirred for 5 h, concentrated under vacuum, suspended in dichloromethane and stirred for one day at room temperature. After filtration, pure acid 4 (1.13 g; 79% yield) was obtained as a beige solid.

Workup

  1. stirringthe mixture stirred at the same temperature for 12 h
  2. stirringstirred for 5 h
  3. concentrationconcentrated under vacuum
  4. stirringstirred for one day at room temperature
  5. filtrationAfter filtration

Sources & evidence

ORD record
ord-56ede8be54b54a6daa5ab04d02a5d6c7
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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