Hydrochloric Acid → Methyl 3-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate

HRID 1874663Notes

Reaction equation

HRID 1874663 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21].Cl>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 58054508Methyl 3-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-hydroxybenzoate (Aldrich) (1.52 g, 10 mmol) and K2CO3 (1.38 g, 10 mmol) in DMF (10 mL) was stirred for 1 h. 2-Chloro-N,N-dimethylacetamide (Merck) (1.03 mL, 10 mmol) was added and the mixture was stirred for 1 h at RT and then stood at RT for 6 days. The mixture was then acidified with 2M HCl and extracted with EtOAc. The aqueous layer was extracted twice more with EtOAc and the combined organic solutions were washed with 2M HCl (×3), aq. sat NaHCO3, brine, dried (MgSO4) and evaporated under reduced pressure to give the title compound (2.22 g, 94%) as a white solid. LCMS (System A) RT=0.80 min, 91%, ES+ve m/z 238 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. waitstood at RT for 6 days
  3. extractionextracted with EtOAc
  4. extractionThe aqueous layer was extracted twice more with EtOAc
  5. washthe combined organic solutions were washed with 2M HCl (×3)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8596ca701f9541468ba0d7e0a0603f09
Source dataset
uspto-grants-2012_11
Patent number
US08304446B2

Reaction notes

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