2,4-Dichloroaniline → 4-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 989344

Reaktionsgleichung

Reaktionsgleichung von HRID 989344
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:29]#[N:30]>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:29]#[N:30]

Komponenten

5

Edukt 3

HCID 111232,4-DichloroanilineHCID 24758Sodium hydrideHCID 98351404-Chloro-7-methoxybenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 219563924-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrileAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

According to the procedure of Example 14, a reaction mixture of 657.8 mg (4.06 mmol) of 2,4-dichloroaniline and 162.4 mg (4.06 mmol) of sodium hydride in 18 mL of anhydrous DMF is stirred at room temperature for 0.5 hour. To the mixture is added 494.0 mg (1.84 mmol) of 4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile. The resulting mixture is heated at 55° C. for 1 hour. After work up, 624.6 mg (86.2%) of 4-(2,4-dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile is obtained as a yellow solid, mp 215-217° C.

Aufarbeitung

  1. temperatureThe resulting mixture is heated at 55° C. for 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-5ba700de3a0949408425f35b46cbb269
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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