Reaktion #82511

Reaktionsgleichung

HOBt

2-quinaldic acid

EDC

→

quinoline

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 100 ml RBF equipped with magnetic stir bar and N2 inlet
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigeroom temperature overnight
4. 4
   workup.ADDITIONThe reaction was poured into sat. bicarb
5. 5
   Extraktionextracted with 2×65 mL ethyl acetate
6. 6
   WaschenThe combined organics were washed with 5% aq. citric acid, brine
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated to 1.4 g crude foam
9. 9
   SonstigePurification by flash chromatography on silica gel (100% ethyl acetate)

Vorschrift

A 100 ml RBF equipped with magnetic stir bar and N2 inlet was charged with 356 mg (2.06 mmol, 1 eq) 2-quinaldic acid in 10 ml dry DMF. The solution was cooled to 0° C. and 415 mg (3.07 mmol, 1.5 eq) HOBt was added followed by 415 mg EDC (2.16 mmol, 1.05 eq). The reaction was stirred 2 hours at 0° C. when 1.1 g (2.06 mmol, 1 eq) of free asparagine amine in 10 ml dry DMF was added. The reaction was stirred at 0° C. for 2 hours then room temperature overnight. The reaction was poured into sat. bicarb and extracted with 2×65 mL ethyl acetate. The combined organics were washed with 5% aq. citric acid, brine, dried and concentrated to 1.4 g crude foam. Purification by flash chromatography on silica gel (100% ethyl acetate) yielded 850 mg (61%) of quinoline adduct.

Quelle