8-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid → 8-bromo-N-(4-methoxybenzyl)quinolin-4-amine

HRID 1469740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469740
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8](C(O)=O)=[C:7]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Komponenten

3

Edukt 1

HCID 866922348-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid

Produkt 1

HCID 866922358-bromo-N-(4-methoxybenzyl)quinolin-4-amineAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid (1.0 g, 2.58 mmol) in diphenyl ether (5 mL) was heated at 240° C. for 30 min. Then petroleum ether was added to the reaction mixture at rt and the precipitated solid was filtered and dried to afford 900 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.38 (d, J=5.4 Hz, 1H), 8.34-8.31 (d, J=9.0 Hz, 1H), 8.06 (t, 1H), 8.02-7.99 (d, J=7.5 Hz, 1H), 7.37-7.29 (m, 3H), 6.90-6.87 (d, J=8.4 Hz, 2H), 6.44 (d, J=5.1 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 3.71 (s, 3H).

Aufarbeitung

  1. filtrationthe precipitated solid was filtered
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-181b20f5156041019c5acbad86612801
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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