Lithium hydroxide, monohydrate → 4-Cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792816
O.[OH-].[Li+].[CH:4]1([C:7]2[C:8]([C:22]([O:24]C)=[O:23])=[CH:9][N:10]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14][CH:13]=3)[CH:11]=2)[CH2:6][CH2:5]1>O1CCCC1.O>[C:22]([C:8]1[C:7]([CH:4]2[CH2:6][CH2:5]2)=[CH:11][N:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:9]=1)([OH:24])=[O:23]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 22024972HCID 22024972, Verbindung

Produkt 1

HCID 220249384-Cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.63 g (15 mmol) of lithium hydroxide monohydrate is added, at a temperature in the region of 20° C., to 1.3 g (4.4 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring for 26 hours at the reflux temperature of the solvent, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 20 mL of water and then triturated with 15 mL of 1 N hydrochloric acid. After the solid residue has been filtered off and dried at a temperature in the region of 50° C. at atmospheric pressure, 1.05 g of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole are obtained in the form of a cream-colored solid melting at 195° C.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customtriturated with 15 mL of 1 N hydrochloric acid
  3. filtrationAfter the solid residue has been filtered off
  4. dry with materialdried at a temperature in the region of 50° C. at atmospheric pressure, 1.05 g of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole

Quellen und Nachweise

ORD-Eintrag
ord-85bef526f5de461aa02d64133e4662c8
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078414B2

Notizen zur Reaktion

Wird geladen…