Hydrochloric Acid → HCID 66877163, compound

HRID 1964035Notes

Reaction equation

HRID 1964035 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH2:7][C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[O:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[CH2:7][C:6]1[CH:5]=[C:4]([CH:15]=[CH:14][CH:13]=1)[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66877414HCID 66877414, compound

Product 1

HCID 66877163HCID 66877163, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.85 g (4.18 mmol) of 2-(3-nitrobenzyl)furan, 1.21 g (21.8 mmol) of reduced iron, and 1 mL of 1N hydrochloric acid were heated under reflux in 10 mL of ethanol for 3.5 hours. After cooling the reaction solution, an aqueous sodium bicarbonate solution was added to alkalify the reaction solution; and filtration through a glass filter, which was covered by celite, was conducted. The filtrate was condensed, and the resulting product was separated and purified using silica gel column chromatography, thereby giving 0.72 g of 3-(furan-2-ylmethyl)aniline (yield: 99%).

Workup

  1. temperatureAfter cooling the reaction solution
  2. filtrationand filtration through a glass
  3. filtrationfilter
  4. customcondensed
  5. customthe resulting product was separated
  6. custompurified

Sources & evidence

ORD record
ord-91b7d70b6bee4deebcf5d416d446c4fb
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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