Hydrochloric Acid → 3-(Furan-2-ylmethoxy)aniline

HRID 1964051Notes

Reaction equation

HRID 1964051 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([N+:14]([O-])=O)[CH:11]=[CH:12][CH:13]=1.Cl.[OH-].[Na+]>C(O)C.[Fe]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[NH2:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 668768842-[(3-Nitrophenoxy)methyl]furan

Product 1

HCID 610355843-(Furan-2-ylmethoxy)anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

830 mg (3.8 mmol) of 3-(furan-2-ylmethyl oxy)nitrobenzene was dissolved in 10 mL of ethanol. 1.1 g (19.70 mmol) of iron and 1 mL of 1N hydrochloric acid (1.0 mmol) were added thereto and heated under reflux for 2 hours. After cooling the reaction solution to room temperature, 1.5 mL of 1N sodium hydroxide was added dropwise, and filtration through celite was carried out. The filtrate was condensed, and ethyl acetate and water were added to the filtrate to separate the solution into organic layer and aqueous layer. The organic layer was separated, washed with a saturated sodium chloride solution, and dried over magnesium sulfate. Thereafter, filtration was carried out, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give 3-(furan-2-ylmethoxy)aniline (yield: 86%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. filtrationfiltration through celite
  4. customcondensed, and ethyl acetate and water
  5. additionwere added to the filtrate
  6. customto separate the solution into organic layer and aqueous layer
  7. customThe organic layer was separated
  8. washwashed with a saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationThereafter, filtration
  11. customcondensed
  12. customThe resulting crude product was separated
  13. custompurified

Sources & evidence

ORD record
ord-1a0a5944ad134b51b0bedd0d2bcec116
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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