Morpholine → 4-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(morpholin-4-yl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 2213805

Reaktionsgleichung

Reaktionsgleichung von HRID 2213805
[Cl:1][C:2]1[C:30]([O:31][CH3:32])=[CH:29][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23]Cl)[C:18]([O:25][CH3:26])=[CH:17][C:14]=4[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:27]#[N:28])=[C:4]([CH3:33])[CH:3]=1.[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH2:57][CH2:58]Cl)=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1.C([O-])(=O)C.[Na+].[NH:72]1[CH2:77][CH2:76][O:75][CH2:74][CH2:73]1>>[Cl:1][C:2]1[C:30]([O:31][CH3:32])=[CH:29][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23][N:72]5[CH2:77][CH2:76][O:75][CH2:74][CH2:73]5)[C:18]([O:25][CH3:26])=[CH:17][C:14]=4[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:27]#[N:28])=[C:4]([CH3:33])[CH:3]=1.[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH2:57][CH2:58][N:72]5[CH2:77][CH2:76][O:75][CH2:74][CH2:73]5)=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 517045Sodium AcetateHCID 115113674-(4-Chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116702254-(4-Chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

Produkt 2

HCID 53304264-(4-Chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrileHCID 53304354-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(morpholin-4-yl)ethoxy]benzo[g]quinoline-3-carbonitrileAusbeute 23 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 318 mg (0.66 mmol) of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 100 mg of sodium acetate and 5 mL of morpholine is stirred and heated to 130° C. using an oil bath. After 30 minutes the reaction is allowed to cool to room temperature. The reaction mixture is concentrated in vacuo and the residue purified by silica gel chromatography, eluting with 95:5 methylene chloride/methanol to yield 82 mg (23%) of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow wax and 153 mg of 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 191–194° C. dec.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 95:5 methylene chloride/methanol

Quellen und Nachweise

ORD-Eintrag
ord-59c991ff5ead4206a69730ba02af0b29
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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