Hydrochloric Acid → {4-[(E)-2-(4-aminophenyl)vinyl]phenyl}amine

HRID 257592

反応式

HRID 257592 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.Cl>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[CH:8][CH:9]=1

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 974991-Nitro-4-[2-(4-nitrophenyl)ethenyl]benzene

生成物 1

HCID 92134{4-[(E)-2-(4-aminophenyl)vinyl]phenyl}amine

試薬・触媒・溶媒 3

HCID 23925Iron触媒2 回HCID 702Ethanol溶媒2 回HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A portion (20.27 grams, 0.075 mole) of 4,4'-dinitrostilbene from A above, concentrated hydrochloric acid (150 milliliters) and ethanol (300 milliliters) are added to a beaker and heated to provide a 60° C. stirred solution. Over the next eight hour period, 325 mesh powdered iron is added to the reaction mixture in aliquots until a total of 33-51 grams (0.60 mole) has been added. After completion of the iron addition, the mixture is heated for 16 hours at 60° C. then diluted with ethanol (250 milliliters) and deionized water (250 milliliters). After cooling to 25° C. , the product is filtered. The resultant solution is treated with 50% aqueous sodium hydroxide sufficient to induce precipitation of a pale tan colored product which is recovered by filtration. The recovered filter cake is washed with deionized water (500 milliliters) then dried in a vacuum oven at 100° C. and 2 mm Hg to a constant weight of 11.3 grams. The product is recovered as a pale tan colored solid. Fourier transform infrared spectrophotometric analysis of a potassium chloride pellet of the product confirms the product structure: Disappearance of the absorbances observed for the conjugated nitro group, appearance of --NH2 stretching absorbances at 3436 (3462 shoulder) and 3356 (3376 shoulder) cm-1, a --NH2 bending absorbance at 1616 cm-1 (1603 cm-1 shoulder due to aromatic ring absorbance) , an out-of-plane C--H deformation at 970 cm-1 due to the trans substituted ethylene group and a C--H out-of-plane bending vibration at 832 cm-1 due to the paradisubstituted aromatic rings. Proton nuclear magnetic resonance spectroscopy further confirms the product structure.

後処理

  1. temperatureheated
  2. customto provide a 60° C.
  3. customOver the next eight hour period, 325 mesh
  4. additionis added to the reaction mixture in aliquots until a total of 33-51 grams (0.60 mole)
  5. additionhas been added
  6. temperatureAfter cooling to 25° C.
  7. filtrationthe product is filtered
  8. additionThe resultant solution is treated with 50% aqueous sodium hydroxide sufficient
  9. customprecipitation of a pale tan colored product which
  10. filtrationis recovered by filtration
  11. filtrationThe recovered filter cake
  12. washis washed with deionized water (500 milliliters)
  13. customthen dried in a vacuum oven at 100° C.
  14. customThe product is recovered as a pale tan colored solid

出典と根拠

ORDレコード
ord-65c331bbd45a4704b7c4309647775dc3
出典データセット
uspto-grants-1993_11
特許番号
US05262509

関連ノート

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