Hydrochloric Acid → 1-Amino-4(1,8-nonadiene-5-yloxy)benzene

HRID 876197Notes

Reaction equation

HRID 876197 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([CH2:16][CH2:17][CH:18]=[CH2:19])[CH2:12][CH2:13][CH:14]=[CH2:15])=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-].[Na+]>[Fe].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH:11]([CH2:16][CH2:17][CH:18]=[CH2:19])[CH2:12][CH2:13][CH:14]=[CH2:15])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867088781-Nitro-4-(1,8-nonadiene-5-yloxy)benzene

Product 1

HCID 867088791-Amino-4(1,8-nonadiene-5-yloxy)benzeneYield 688.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A 300 ml-capacity three neck flask containing a stirring bar and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask. 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) (4.01 g, 1.4 mmol), an iron powder (3.13 g, 5.6 mmol), and ethanol (50%, 10 ml) were introduced into the flask, and the mixture thus obtained was started to be stirred while heating the flask in an oil bath. Further, HCl (0.52 ml) and ethanol (50%, 2.5 ml) were slowly added to the mixture, which was then stirred for 2 hours. Thereafter, an aqueous sodium hydroxide solution was added to the mixture to stop the reaction, and an organic layer was extracted with ethyl acetate. This organic layer was dried over Na2SO4 and filtered, a solvent was distilled of under reduced pressure, and the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1). Thus, 1-amino-4(1,8-nonadiene-5-yloxy)benzene (12) (2.39 g, 9.64×10−3 mol, yield: 69%) was obtained as an intended compound.

Workup

  1. additionA 300 ml-capacity three neck flask containing a stirring bar
  2. customconnected to a condenser
  3. customwas sufficiently dried
  4. customthe mixture thus obtained
  5. temperaturewhile heating the flask in an oil bath
  6. stirringwas then stirred for 2 hours
  7. customthe reaction
  8. extractionan organic layer was extracted with ethyl acetate
  9. dry with materialThis organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. distillationa solvent was distilled of under reduced pressure
  12. customthe organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6eb22a9fa07b4162a0af5932d1b74519
Source dataset
uspto-grants-2015_03
Patent number
US08987044B2

Reaction notes

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