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

HRID 1009909Notes

Reaction equation

HRID 1009909 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-a1bc50762cc5449aa1bc76a9d368e6e5
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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