Hydrochloric Acid → 5-(Aminomethyl)-2-(2-methoxyethoxy)phenol

HRID 2236571Notes

Reaction equation

HRID 2236571 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:7]([OH:16])[CH:6]=1.Cl>CCO.[Pd]>[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:7]([OH:16])[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 722508733-hydroxy-4-(2-methoxyethoxy)benzaldehyde O-methyloxime

Product 1

HCID 426255215-(Aminomethyl)-2-(2-methoxyethoxy)phenolYield 68.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 3-hydroxy-4-(2-methoxyethoxy)benzaldehyde O-methyloxime (0.75 g, 3.33 mmol) in 10 mL of EtOH is added 1 mL of 12 N HCl and palladium on carbon. The reaction mixture is hydrogenated for 4 h. After removal of solid by filtration, solvent is evaporated to give yellow oil. Colorless solid is afforded after the oil is washed 5 times with EtOAc. Recrystallization from MeOH/EtOAc afforded 0.45 g (68.5% yield) of colorless solid: mp: 89-90° C.; MS (ESI) m/z 198.1 (M+H)+1

Workup

  1. customAfter removal of solid
  2. filtrationby filtration, solvent
  3. customis evaporated
  4. customto give yellow oil
  5. customColorless solid is afforded after the oil
  6. washis washed 5 times with EtOAc
  7. customRecrystallization from MeOH/EtOAc

Sources & evidence

ORD record
ord-9230277c91424f8785aae9646b8ae5d4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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