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Hydrochloric Acid → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-[2-(2-methoxyphenoxy)ethyl]amine

HRID 721635
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 721635
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=O)[CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[CH:18][CH:17]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21890817HCID 21890817, Verbindung

Produkt 1

HCID 21891117N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-[2-(2-methoxyphenoxy)ethyl]amineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N1-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-2-(2-methoxyphenoxy)acetamide (200 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A 1 M solution (1.3 ml) of a borane-tetrahydrofuran complex in tetrahydrofuran was then added to the solution, and the mixture was stirred with heating under reflux for 2 hr. The reaction solution was cooled to 0° C. and was adjusted to pH=1 by the addition of 1 N hydrochloric acid, followed by stirring with heating under reflux for 30 min. The reaction solution was cooled to 0° C., was adjusted to pH=12 by the addition of a 1 N aqueous sodium hydroxide solution, and was extracted with chloroform. After the concentration of the extract, the residue was purified on a column using chloroform/methanol to give the title compound (155 mg, yield 80%). Mass spectrometry value (ESI-MS, m/z): 447 (M++1)

Aufarbeitung

  1. customto prepare a solution
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hr
  4. stirringby stirring
  5. temperaturewith heating
  6. temperatureunder reflux for 30 min
  7. temperatureThe reaction solution was cooled to 0° C.
  8. extractionwas extracted with chloroform
  9. customAfter the concentration of the extract, the residue was purified on a column

Quellen und Nachweise

ORD-Eintrag
ord-9deac615873845abac88885a8b01cc2d
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07135466B2

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