Hydrochloric Acid → 2-(4-Chlorophenyl)-6-hydroxypyrimidine-4-carboxylic acid

HRID 249661

Reaktionsgleichung

[Na].[C:2]([O:12]CC)(=[O:11])[CH2:3][C:4]([C:6]([O:8]CC)=O)=O.[OH-].[Na+].Cl.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:27])[NH2:26])=[CH:21][CH:20]=1.Cl>O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:27][C:6](=[O:8])[CH:4]=[C:3]([C:2]([OH:12])=[O:11])[N:26]=2)=[CH:21][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a mixture of diethyl oxalacetate sodium salt (123.2 g, 586 mmol) in water (750 mL) was slowly added aqueous sodium hydroxide (50%, 47 g, 586 mmol). After 1 h the solids had dissolved. 4-Chlorobenzenecarboximidamide monohydrochloride (111.95 g, 586 mmol) was then added, and the mixture was heated at 70° C. overnight. After cooling to room temperature concentrated hydrochloric acid was slowly added (causing foaming) until the pH was lowered to 1.5. The solid was isolated by filtration and washed with water and methanol. The solid was then triturated twice with hot methanol, washed repeatedly with 1 N hydrochloric acid, then once with methanol and dried to afford the title compound (66.07 g).

Aufarbeitung

dissolutionAfter 1 h the solids had dissolved
additionwas slowly added (causing foaming) until the pH
customThe solid was isolated by filtration
washwashed with water and methanol
customThe solid was then triturated twice with hot methanol
washwashed repeatedly with 1 N hydrochloric acid
dry with materialonce with methanol and dried

Quellen und Nachweise

ORD-Eintrag: ord-8e1ddbf19327444aa4e98e53193ac2aa
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863220B2

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