Reaktion #451557

Reaktionsgleichung

sodium hydride

5-fluoro-2-hydroxybenzamide

1-methyl-3-pyrrolidinol methane sulfonate

→

off-white crystals

Ausbeute 42.0%

5-Fluoro-2-(1-methyl-3-pyrrolidinyloxy)benzamide

Ausbeute 42.0%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then heated to 100° C. for 18 hr
2. 2
   SonstigeThe dimethylformamide was removed by rotary evaporation at 70° C.
3. 3
   Waschenwashed with 2×50 ml of 1N sodium hydroxide and 50 ml of water
4. 4
   ExtraktionThe organic phase was extracted with 2×50 ml of 1N hydrochloric acid
5. 5
   WaschenThe combined aqueous extracts were washed with 50 ml of methylene chloride
6. 6
   Extraktionextracted into 2×50 ml of methylene chloride
7. 7
   TrocknenThe combined organic extracts were dried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated by rotary evaporation
10. 10
    SonstigeThe residual oil was crystallized from hexane

Vorschrift

To a suspension of 0.44 g (60% in oil, 0.011 mole) of sodium hydride in 10 ml of dimethylformamide was added 1.55 g (0.01 mole) of 5-fluoro-2-hydroxybenzamide in 10 ml of dimethylformamide under nitrogen atmosphere at room temperature. The reaction mixture was heated to 60° C. and 1.80 g (0.01 mole) of 1-methyl-3-pyrrolidinol methane sulfonate (ester) was added. The reaction mixture was then heated to 100° C. for 18 hr. The dimethylformamide was removed by rotary evaporation at 70° C., 0.5 mm Hg. The residue was taken up in 200 ml of methylene chloride, washed with 2×50 ml of 1N sodium hydroxide and 50 ml of water. The organic phase was extracted with 2×50 ml of 1N hydrochloric acid. The combined aqueous extracts were washed with 50 ml of methylene chloride, made basic with concentrated sodium hydroxide and extracted into 2×50 ml of methylene chloride. The combined organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residual oil was crystallized from hexane to give 1.0 g of off-white crystals, m.p. 90°-93° C.

Quelle