Triphenylphosphine → 4-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholine

HRID 393599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393599
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([OH:45])=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][CH:34]=1.[O:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][CH2:54]O)[CH2:48][CH2:47]1>C(Cl)Cl>[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([O:45][CH2:54][CH2:53][CH2:52][N:49]3[CH2:50][CH2:51][O:46][CH2:47][CH2:48]3)=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][CH:34]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 1995763-Morpholino-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Produkt 1

HCID 222652574-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholineAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (120 μl, 0.76 mmol) was added dropwise to a solution of triphenylphosphine (200 mg, 0.76 mmol), 4-chloro-7-hydroxy-6-methoxyquinoline (100 mg, 0.47 mmol), 3-morpholino-1-propanol (75 mg, 0.52 mmol), (Tet. Lett. 1994, 35, 1715), in methylene chloride (5 ml). The mixture was stirred for 4 hours at ambient temperature, the solvent was removed by evaporation to dryness and purified by column chromatography eluting with methylene chloride/methanol (9/1) to give 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline (105 mg, 66%).

Aufarbeitung

  1. customthe solvent was removed by evaporation to dryness
  2. custompurified by column chromatography
  3. washeluting with methylene chloride/methanol (9/1)

Quellen und Nachweise

ORD-Eintrag
ord-7c74bfc254114792be1064c4897e364f
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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