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

HRID 876197ノート

反応式

HRID 876197 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6eb22a9fa07b4162a0af5932d1b74519
出典データセット
uspto-grants-2015_03
特許番号
US08987044B2

反応ノート

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