Ethyl 2-aminoquinoline-3-carboxylate → Ethyl 3,4-dihydro-4-oxopyrimido(4,5-b)quinoline-2-carboxylate

HRID 442198

Reaktionsgleichung

Reaktionsgleichung von HRID 442198
[C:1]([C:6](=[NH:8])[O-])([O:3][CH2:4][CH3:5])=[O:2].[NH2:9][C:10]1[C:19]([C:20](OCC)=[O:21])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>C(O)C>[N:9]1[C:10]2=[N:11][C:12]3[C:17]([CH:18]=[C:19]2[C:20](=[O:21])[NH:8][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:16][CH:15]=[CH:14][CH:13]=3

Komponenten

4

Edukt 2

HCID 283477Ethyl 2-aminoquinoline-3-carboxylateHCID 227528221-Carbethoxyformimidate

Produkt 1

HCID 135765023Ethyl 3,4-dihydro-4-oxopyrimido(4,5-b)quinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The same compound is obtained by: (a) refluxing equimolar amounts of 1-carbethoxyformimidate and ethyl 2-aminoquinoline-3-carboxylate in ethanol for 3 hours. The reaction mixture is concentrated, the product collected by filtration and recrystallized from hot chloroform; or (b) refluxing equimolar amounts of 1-carbethoxyformamidine and 2-aminoquinoline-3-carboxamide in ethanol for 3-4 hours in the presence of an equimolar amount of sodium ethoxide. The reaction mixture is worked up as described in (a) above.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. filtrationthe product collected by filtration
  3. customrecrystallized from hot chloroform
  4. temperatureor (b) refluxing equimolar amounts of 1-carbethoxyformamidine and 2-aminoquinoline-3-carboxamide in ethanol for 3-4 hours in the presence of an equimolar amount of sodium ethoxide

Quellen und Nachweise

ORD-Eintrag
ord-0de48ff5924342b4a28a9dc891b6be5d
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04044134

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