Sodium Iodide → 4-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 2213808

Reaktionsgleichung

Reaktionsgleichung von HRID 2213808
[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21]Cl)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26].[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56]Cl)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[CH3:67][N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1.[I-].[Na+]>COCCOC>[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56][N:71]4[CH2:72][CH2:73][N:68]([CH3:67])[CH2:69][CH2:70]4)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21][N:71]4[CH2:72][CH2:73][N:68]([CH3:67])[CH2:69][CH2:70]4)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 115696394-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116633894-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

Produkt 2

HCID 53304294-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrileHCID 53304384-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 0.4 g (0.8 mmol) of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 1.25 ml (11.27 mmol) of 1-methyl piperazine and 0.05 g of sodium iodide in 2.0 mL of ethylene glycol dimethyl ether is heated at 90° C. for 2 hours under nitrogen. The mixture is cooled, the solvent is removed in vacuo and the resulting residue is stirred with saturated solution of sodium bicarbonate. The crude solid is collected by filtration, washed with water, and dried in vacuo. Purification is carried out by silica gel chromatography, eluting with a gradient of 92:8 to 85:15 methylene chloride/methanol to yield 0.149 g of 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 141–150° C. and 0.203 g of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 132–135° C.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. customthe solvent is removed in vacuo
  3. filtrationThe crude solid is collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customPurification
  7. washeluting with a gradient of 92:8 to 85:15 methylene chloride/methanol

Quellen und Nachweise

ORD-Eintrag
ord-45665d7ae8fb445e93979ea5d91cf271
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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