Hydrochloric Acid → 3-(Dimethylcarbamoyl)benzoic acid

HRID 1361798Notes

Reaction equation

HRID 1361798 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10]C)=[O:9])=[O:4].O.[OH-].[Li+].Cl>CO.O>[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([OH:10])=[O:9])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 12810605Methyl 3-(dimethylcarbamoyl)benzoate

Product 1

HCID 198309083-(Dimethylcarbamoyl)benzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-(N,N-dimethylcarbamoyl)benzoate (2.30 g, 11.1 mmol) obtained in Step 1 was dissolved in a mixed solvent (1:1) (50 mL) of methanol and water, and lithium hydroxide monohydrate (932 mg, 22.2 mmol) was added thereto, followed by stirring at room temperature for 1 hour. 3 mol/L hydrochloric acid was added to the reaction mixture to adjust the pH to 3, and the precipitated solid was collected by filtration to afford 3-(N,N-dimethylcarbamoyl)benzoic acid (2.12 g, 99%).

Workup

  1. additionwas added
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-88fbbd6035b94f09ba812cbce1c66b01
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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