Reaktion #7726

Reaktionsgleichung

sodium methoxide

7-(3-Fluoro-benzyloxy)-2-methyl-3H-quinazolin-4-one

2-amino-4-(3-fluoro-benzyloxy)-benzoic acid

ethyl acetamidate HCl

ethyl acetamidate HCl

sodium methoxide

→

title compound

Ausbeute 97.0%

2-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamide

Ausbeute 97.0%

Lösungsmittel

water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated
2. 2
   Temperaturunder reflux for 19 h
3. 3
   Temperaturthe resulting mixture heated for another 1 h
4. 4
   Filtrationfiltered off

Vorschrift

7-(3-Fluoro-benzyloxy)-2-methyl-3H-quinazolin-4-one: To a mixture of 2-amino-4-(3-fluoro-benzyloxy)-benzoic acid (2.0 g, 7.7 mmol) and ethyl acetamidate HCl (1.9 g, 15.3 mmol) in methanol (30 mL) was added sodium methoxide (5.4 M, 0.83 g, 15.3 mmol) and the resulting mixture was heated under reflux for 19 h. After this time ethyl acetamidate HCl (1.9 g, 15.3 mmol) and sodium methoxide (5.4 M, 0.83 g, 15.3 mmol) was added and the resulting mixture heated for another 1 h. After cooling to rt the mixture was poured into water (40 mL) and then the resulting precipitate was stirred for 2 h, and filtered off to afford the title compound (2.1 g, 97%) as an off-white solid. MS: m/e=283.1 (M−H).

Quelle