Acetic Acid → 3-Methyl-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamide

HRID 1064354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064354
[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[C:5]([N:7](C(=O)C1C=CC=C(C)C=1)[C:8]1[C:17]([C:18]#[N:19])=[C:16]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[OH-].[K+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[C:5]([NH:7][C:8]1[C:17]([C:18]#[N:19])=[C:16]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 11156487HCID 11156487, Verbindung

Produkt 1

HCID 99085263-Methyl-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamideAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To the solution of 5 g of 3-methyl-N-(3-methylbenzoyl)-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamide in 80 ml of acetonitrile 20 ml of 1N methanolic potassium hydroxide solution are added. The reaction mixture is refluxed for 3 minutes, then 3 ml of glacial acetic acid is added to it, then it is neutralized with 50 ml of 1M sodium hydrogen carbonate solution and the resulting crystals are filtered off. The white crystalline material is recrystallized from 130 ml of acetonitrile to give 3.1 g of the title compound of general formula (I). Mp.: 230° C.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 3 minutes
  2. filtrationthe resulting crystals are filtered off
  3. customThe white crystalline material is recrystallized from 130 ml of acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-749a0ad361094b509f3cd42dd59d798f
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969723B2

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