Methyl cyanoacetate → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

HRID 266120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266120
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])#[N:29]>O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:8]2[C:7]3[C:6](=[CH:23][C:22]([O:24][CH3:25])=[C:21]([O:26][CH3:27])[CH:20]=3)[N:5]=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[N:29]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Komponenten

5

Edukt 3

HCID 7747Methyl cyanoacetateHCID 6451240Aluminum(III) ChlorideHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Produkt 1

HCID 212240726,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Aluminium chloride powder (5.3 g) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (6.3 g) and methyl cyanoacetate (23 ml), and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The residue was subjected to column chromatography on silica gel. The fractions eluted with hexane-ethyl acetate (4:1, v/v) gave methyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline-2-acetate. This compound was recrystallized from acetone. Colorless needles, mp. 152°-153° C.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. washThe fractions eluted with hexane-ethyl acetate (4:1

Quellen und Nachweise

ORD-Eintrag
ord-41f7c6e978974dc5ae6e3a2c6dd0184f
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

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