Reaktion #44300

Reaktionsgleichung

N,O-dimethyl hydroxylamine

quinoline-6-carboxylic acid

carbonyl diimidazole

→

quinoline-6-carboxylic acid methoxy-methyl-amide

Ausbeute 97.0%

Lösungsmittel

EtOAc

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred at ambient temperature for 16 hours
2. 2
   SonstigeThe organic layer was separated
3. 3
   Extraktionthe aqueous layer was extracted with EtOAc (5×100 mL)
4. 4
   Waschenwashed with water (3×100 mL), brine (2×100 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To a solution of quinoline-6-carboxylic acid (10 g, 57.75 mmol) in DMF (200 mL) was added carbonyl diimidazole (10.3 g, 62.5 mmol) under nitrogen. The reaction was stirred for 1 hour. To the solution was added N,O-dimethyl hydroxylamine (5.6 g, 57.75 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was diluted with EtOAc (150 mL) and water (150 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (5×100 mL). The organics were combined and washed with water (3×100 mL), brine (2×100 mL), dried over Na2SO4, filtered and concentrated to give quinoline-6-carboxylic acid methoxy-methyl-amide (11.97 g, 97% yield).

Quelle