Hydrochloric Acid → 2-Hydroxy-N,N-dimethylbenzamide

HRID 2294138Notes

Reaction equation

HRID 2294138 reaction equation
C([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7](Cl)=[O:8])(=O)C.[CH3:14][NH:15][CH3:16].[OH-].[Na+].Cl>C1COCC1.O>[OH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:15]([CH3:16])[CH3:14])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 14798Sodium HydroxideHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 745002-Hydroxy-N,N-dimethylbenzamideYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of acetylsalicyloyl chloride (3.4 g, 17 mmol) in 120 mL of THF was added dropwise to 30 mL of 40% aqueous dimethylamine (66 mmol). The mixture was stirred at room temperature for 3 hours and then sodium hydroxide (4 g, 0.1 mmol) was added. The mixture was stirred at room temperature for approximately 60 hours and then poured into 20 mL of water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated. The residue was purified on silica gel by flash chromatography eluting with 6% methanol/methylene chloride to give 2-hydroxy-N,N-dimethylbenzamide (2.4 g, 14.53 mmol), m.p. 145°-152° C.

Workup

  1. stirringThe mixture was stirred at room temperature for approximately 60 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel by flash chromatography
  6. washeluting with 6% methanol/methylene chloride

Sources & evidence

ORD record
ord-5e6e1d1d4b784d798b79c12835b3d6e3
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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