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

HRID 14124Notes

Reaction equation

HRID 14124 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-1253b6bd201640669ae0fb77cdf1d491
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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