Water → HCID 21085670, compound

HRID 14150Notes

Reaction equation

HRID 14150 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[C:10]([O:12]C)=[O:11])[CH3:5].O.[OH-].[Li+]>CO.O1CCCC1>[OH:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[C:10]([OH:12])=[O:11])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086146HCID 21086146, compound

Product 1

HCID 21085670HCID 21085670, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-{[(2-hydroxyethyl)(methyl)amino]methyl}-5-methylbenzoate (180 mg, 0.72 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (302 mg, 7.2 mmol), and the reaction mixture is stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure, dissolved in methylene chloride, filtered, and concentrated under reduced pressure to provide the title compound. ESI MS m/z 224 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-167c4b3f190649a88273d05fff4e636a
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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