Stannane, hydroxytrimethyl- → 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acid

HRID 1519800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519800
[OH-].C[Sn+](C)C.[C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14](=[O:23])[N:15]2[CH2:18][C:19]([O:21]C)=[O:20])=[CH:10][CH:9]=1)#[N:7]>ClCCCl.ClCCl>[C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14](=[O:23])[N:15]2[CH2:18][C:19]([OH:21])=[O:20])=[CH:10][CH:9]=1)#[N:7]

Komponenten

5

Edukt 2

HCID 11217597Stannane, hydroxytrimethyl-HCID 68785451methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate

Produkt 1

HCID 687822352-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trimethyl tin hydroxide (0.388 g, 2.14 mmol) was added to a solution of methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate (0.104 g, 0.429 mmol) in 1,2-dichloroethane (5 mL) and the resulting suspension was stirred at reflux for 4 h. The reaction mixture was diluted with dichloromethane and washed with 1N aqueous HCl. Filtration of the organic phase provided 87 mg (89%) of 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acid. Retention time (min)=0.987, method [1], MS(ESI) 229.1 (M+H).

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. washwashed with 1N aqueous HCl
  3. filtrationFiltration of the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-4bd2a82db49d4b1781eb81451c37ed3f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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