Sodium Bicarbonate → 2-carboxy-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran

HRID 1090786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090786
[C:1]([C:6]1[O:7][C:8]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:21][CH:20]=3)=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)([O:3]CC)=[O:2].C(=O)(O)[O-].[Na+]>C(O)C.O>[C:1]([C:6]1[O:7][C:8]2[C:16]([CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:23][CH:24]=3)=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)([OH:3])=[O:2]

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 19913843HCID 19913843, Verbindung

Produkt 1

HCID 148423732-carboxy-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyranAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

0.74 g of 2-carboethoxy-8-(4-(quinoline-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran and 0.7 g sodium bicarbonate are combined in 50 ml of ethanol and 5 ml of water. After refluxing for 1.5 hours the mixture is concentrated and the residue diluted with ether. The resulting solid is collected, suspended in water and the pH adjusted to 6 with 1 molar hydrochloric acid. The resulting solid is crystallized from aqueous acetic acid, then tetrahydrofuran/hexane to give 0.43 g 2-carboxy-8-(4- (quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran; m.p. 221°-24° C.

Aufarbeitung

  1. temperatureAfter refluxing for 1.5 hours the mixture
  2. concentrationis concentrated
  3. additionthe residue diluted with ether
  4. customThe resulting solid is collected
  5. customThe resulting solid is crystallized from aqueous acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-d50b8d91f5c4412b8e38e27725015535
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082849

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