Hydrochloric Acid → 2-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

HRID 889540Notes

Reaction equation

HRID 889540 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O1CCOCC1.[OH-].[Li+].Cl>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67971274Methyl 2-chloro-5-(pivalamidomethyl)benzoate

Product 1

HCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidYield 77.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add methyl 2-chloro-5-[(2,2-dimethylpropanoylamino)methyl]benzoate (1.05 kg, 3.7 mol), 1,4-dioxane (5.25 L) and water (3.15 L) together and then add lithium hydroxide (407.8 g, 9.6 mol). Stir the resulting suspension at room temperature for one hour. Acidify the mixture to pH 1 with 5 N aqueous HCl in a dropwise fashion at a rate such that the internal temperature does not exceed 30° C. Concentrate the solution to remove approximately 6 L of solvent, and cool the resulting suspension to 10° C. Filter, wash the resulting solid material with water (8 L), and allow to dry on the sinter for 3 h. Collect the solid, and dry the material in a vacuum oven at 40° C. for 48 h to give the title compound as a free-flowing white solid (775 g, 77.7%). MS (m/z) (35Cl/37Cl) 270/272 (M+1).

Workup

  1. customdoes not exceed 30° C
  2. concentrationConcentrate the solution
  3. customto remove approximately 6 L of solvent
  4. temperaturecool the resulting suspension to 10° C
  5. filtrationFilter
  6. washwash the resulting solid material with water (8 L)
  7. customto dry on the sinter for 3 h
  8. customCollect the solid
  9. customdry the material in a vacuum oven at 40° C. for 48 h

Sources & evidence

ORD record
ord-f8271c7d666841698eaedbed06ae13b6
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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