Ammonium Hydroxide → 4-(2,4-Dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile

HRID 989346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989346
[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:21]#[N:22].Cl.N1C=CC=CC=1.[OH-].[NH4+]>>[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:21]#[N:22]

Komponenten

4

Edukt 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 219563924-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 219564804-(2,4-Dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile

Reaktionsbedingungen

Temperatur
215 °C

Versuchsvorschrift

A reaction mixture of 566.5 mg (1.44 mmol) of 4-(2,4-dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile and 10 g of pyridine hydrochloride is stirred at 215° C. for 50 min under nitrogen. After cooling, the mixture is neutralized with 40 mL of a 3% ammonium hydroxide solution and stirred for 0.5 hour. The separated solid is filtered off and washed with water and ether. After drying in vacuo, this yields 527.9 mg (96.5%) of 4-(2,4-dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile as a salmon color solid, mp>300° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. stirringstirred for 0.5 hour
  3. filtrationThe separated solid is filtered off
  4. washwashed with water and ether
  5. customAfter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90151e72988648c6ae3457cf8af9d2ee
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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