Hydrochloric Acid → 3-Benzyloxy-5-hydroxy-N,N-dimethylbenzamide

HRID 1713300Notes

Reaction equation

HRID 1713300 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=1)[C:8](O)=[O:9])(=O)C.C(Cl)(=O)C(Cl)=O.C[O-].[Na+].CO.Cl.[CH3:34][N:35](C)[CH:36]=O>ClCCl.O1CCCC1>[CH2:15]([O:14][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([OH:4])[CH:13]=1)[C:8]([N:35]([CH3:36])[CH3:34])=[O:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 23694274Sodium methanolate methanolHCID 674572213-Acetoxy-5-benzyloxybenzoic acid

Product 1

HCID 674564673-Benzyloxy-5-hydroxy-N,N-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Acetoxy-5-benzyloxybenzoic acid (1.0 g) was suspended in dichloromethane (12 mL), oxalyl chloride (0.49 g), N,N-dimethylformamide (0.01 mL), tetrahydrofuran was added sequentially, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and then dichloromethane was added to the residue. Dimethylamine hydrochloride (0.28 g) and pyridine (0.1 mL) were added to the reaction mixture and stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was dissolved in tetrahydrofuran (15 mL). Sodium methoxide-methanol solution (5.2 mol/L, 1.02 mL) was added to the reaction mixture and stirred at room temperature for 30 minutes. One mol/L hydrochloric acid was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel (eluent: ethylacetate/hexane=1/1) to give the title compound (0.67 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondichloromethane was added to the residue
  3. additionDimethylamine hydrochloride (0.28 g) and pyridine (0.1 mL) were added to the reaction mixture
  4. stirringstirred at room temperature for 24 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue obtained
  7. stirringstirred at room temperature for 30 minutes
  8. extractionthe whole was extracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified by column chromatography on silica gel (eluent: ethylacetate/hexane=1/1)

Sources & evidence

ORD record
ord-2be5c032409a45abb9cb1d65d21aa4c0
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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