4,4'-(Pentamethylenedioxy)-bis-(nitrobenzene) → 1,5-Bis(p-aminophenoxy)pentane

HRID 982598

Reaktionsgleichung

Reaktionsgleichung von HRID 982598
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 2

HCID 5505304,4'-(Pentamethylenedioxy)-bis-(nitrobenzene)HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 141731,5-Bis(p-aminophenoxy)pentaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1,5-bis(4-nitrophenoxy)pentane (32.7 grams, 94.4 mmol; prepared as described in Part A of this Example) and Pd/C 10% (1.00 gram, obtained from Aldrich Chemical Co.) was stirred for 20 hours in tetrahydrofuran (400 milliliters) under 200 pounds per square inch of hydrogen gas. The mixture was then filtered over CELITE, and the solvent was removed by evaporation under reduced pressure. The resulting crude solid was recrystallized from ethanol to afford pure 1,5-bis(4-aminophenoxy)pentane (24.4 grams, 85.1 mmol, 90 percent yield) as small colorless crystals: mp 78-79° C.; IR (KBr) 3433, 3353, 3217, 2949, 2868, 1856, 1632, 1511, 1473, 1396, 1228, 1031, 1002, 825, 517 cm−1; 1H NMR (300 MHz, CDCl3) δ6.76 (d, 4H, 3J=8.8 Hz), 6.64 (d, 4H, 3J=8.8 Hz), 3.92 (td, 4H, 3J=6.4 Hz, 4J=1.4 Hz), 3.40 (s, 4H), 1.82 (q, 4H, 3J=6.8 Hz), 1.62 (q, 2H, 3J=6.8 Hz): 13C NMR (75 MHz, CDCl3) δ151.31, 140.06, 116.51, 115.78, 68.58, 29.32, 22.83; MS (FAB, 3-nitrobenzyl alcohol) m/e 286.7; Anal. Calcd for C17H22N2O2: C, 71.30; H. 7.74; N, 9.78. Found: C, 71.11; H, 8.22; N, 9.85.

Aufarbeitung

  1. customprepared
  2. filtrationThe mixture was then filtered over CELITE
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe resulting crude solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-067a3642de9e4207955a397517fe5891
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06860928B2

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