Water → 4-[(2-Hydroxyethyl)(methyl)amino]benzoic acid

HRID 735733Notes

Reaction equation

HRID 735733 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:16])[C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][CH:6]=1.[OH-].[Na+].O>CO>[OH:1][CH2:2][CH2:3][N:4]([CH3:16])[C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 10242689HCID 10242689, compound

Product 1

HCID 224393304-[(2-Hydroxyethyl)(methyl)amino]benzoic acidYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (10 ml) of ethyl 4-[(2-hydroxyethyl) (methyl)amino]benzoate (500 mg, 2.24 mmol) in methanol was added 1M aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was washed with diethyl ether. 1M Hydrochloric acid (10 ml) was added, and the mixture was extracted with dichloromethane and concentrated under reduced pressure to give the title compound (119 mg, 27%) as a white solid.

Workup

  1. washthe mixture was washed with diethyl ether
  2. addition1M Hydrochloric acid (10 ml) was added
  3. extractionthe mixture was extracted with dichloromethane
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a0c8d71fada4cf9845d226ce55136b9
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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