Sodium Hydroxide → 2-(4-Hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolin

HRID 336736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336736
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[N:6]=[C:7]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([O:23]C(=O)C)=[C:18]([CH3:27])[CH:17]=1)[N:8]2[CH3:15].[OH-].[Na+]>C(O)C>[OH:23][C:19]1[C:20]([CH3:22])=[CH:21][C:16]([CH:7]2[N:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:3]=3[O:2][CH3:1])[N:8]2[CH3:15])=[CH:17][C:18]=1[CH3:27]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66661452Acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinazolin-2-yl)-2,6-dimethyl-phenyl ester

Produkt 1

HCID 866612712-(4-Hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolinAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2,4-dimethoxy-6-methylamino-benzamide (0.28 g, 1.33 mmol) in pyridine (10 mL) was added to acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester (1.1 eq.) and stirred at room temperature for 14 h. The solvent was removed and the reaction mixture was acidified with 1 N HCl and extracted with ethyl acetate. The solvent was removed and the crude was purified by silica gel column chromatography (40 g) employing 1% methanol in dichloromethane to give acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenyl ester (0.34 g, 67%). Acetic acid 4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenyl ester (0.34 g, 0.89 mmol) was dissolved in ethanol (5 mL), 5% aqueous NaOH solution (10 mL) was added dropwise and the mixture was stirred at room temperature for 1.5 h. The compound was extracted with ethyl acetate and washed with ether to give 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-1-methylquinazolin-4(1H-one (0.13 g, 43%). Selected data: MS (ES) m/z: 340.17; MP 188.5-189.1° C.

Aufarbeitung

  1. extractionThe compound was extracted with ethyl acetate
  2. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-eb7652a6711f4c0a80852e09c4f96cb7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889698B2

Notizen zur Reaktion

Wird geladen…