Water → 3-{[(2-Furylmethyl)(methyl)amino]methyl}-5-methylbenzoic Acid

HRID 348916Notes

Reaction equation

HRID 348916 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:13]([O:15]C)=[O:14])[CH3:8].O.[OH-].[Li+]>CO.O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:13]([OH:15])=[O:14])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086145Methyl 3-{[(2-furylmethyl)(methyl)amino]methyl}-5-methylbenzoate

Product 1

HCID 210856693-{[(2-Furylmethyl)(methyl)amino]methyl}-5-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-{[(2-furylmethyl)(methyl)amino]methyl}-5-methylbenzoate (180 mg, 0.66 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (277 mg, 6.6 mmol), and the reaction mixture stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure, dissolved in methylene chloride, filtered, and the filtrate concentrated under reduced pressure to provide the title compound. ESI MS m/z 258 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-c058a9e5c4c6460b9e7adfed34441b4e
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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