Water → 3-Methyl-5-{[methyl(pentyl)amino]methyl}benzoic Acid

HRID 14137Notes

Reaction equation

HRID 14137 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>CO.O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086189Methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate

Product 1

HCID 210858383-Methyl-5-{[methyl(pentyl)amino]methyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate (120 mg, 0.46 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (191 mg, 4.6 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 250 [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-2ae0cf8075094dd783a9be2a344e0efc
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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