Reaktion #42636

Reaktionsgleichung

N-methylisatoic anhydride

HCl

ethylmethanesulfonylacetate

sodium hydride

hydrogen

→

white solids

Ausbeute 48.0%

4-Hydroxy-3-methanesulfonyl-1-methyl-1H-quinolin-2-one

Ausbeute 48.0%

Lösungsmittel

dimethylacetamide

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Temperaturheated overnight at 120° C
3. 3
   TemperaturThe mixture was cooled to room temperature
4. 4
   SonstigeThe solids formed
5. 5
   Filtrationwere filtered
6. 6
   Waschenwashed several times by water

Vorschrift

A solution of ethylmethanesulfonylacetate (3.78 g, 22.74 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 1.07 g, 25 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min and cooled to room temperature. A solution of N-methylisatoic anhydride (4.43 g, 25 mmol) in dimethylacetamide was added slowly and heated overnight at 120° C. The mixture was cooled to room temperature, poured into ice water and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 2.76 g (48%) of white solids. Mp 170° C. 1H NMR (DMSO-d6): δ 3.51 (s, 3H), 3.59 (s, 3H), 7.39 (t, J=7.4 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.84 (t, J=7.0 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H). EIMS m/z 254 (M+1), 276 (M+23). Anal. (C11H11NO4S) C, H, N.

Quelle