Toluene → 4-(2-Fluoro-4-nitrophenyloxy)-6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinoline

HRID 68535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68535
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C1(C)C=CC=CC=1.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 98252-Fluoro-4-nitrophenolHCID 226466304-Chloro-6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinoline

Produkt 1

HCID 866969174-(2-Fluoro-4-nitrophenyloxy)-6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinolineAusbeute 285,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

2-fluoro-4-nitrophenol (36.73 g, 0.234 mol) was added to a dried chlorobenzene (5v/w, 250 mL). The mixture was heated to 145° C. Intermediate VII (12.5 g, 0.039 mol) was added to the reaction solution. The reaction was conducted at this temperature for 20 h. After completion of the reaction, the solvent was evaporated off to produce a grey solid. This solid was dissolved in CH2Cl2, and washed with a satureated saturated K2CO3 solution several times. The organic layer was collected. The solvent was dried off to produce a solid, which is recrystallized with ethanol to produce a yellow solid (49.16 g) in a yield of 71.4%.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated off
  3. customto produce a grey solid
  4. washwashed with a satureated saturated K2CO3 solution several times
  5. customThe organic layer was collected
  6. customThe solvent was dried off
  7. customto produce a solid, which
  8. customis recrystallized with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f066b89403a94d5eaa5d9770d18a2c39
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822465B2

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