Reaktion #1856445

Reaktionsgleichung

3-(N,N-dimethylamino)-pyridine

5-chloroquinolin-8-oxyacetic acid

2-allyloxy-1-methylethanol

dicyclohexylcarbodiimide

→

2-allyloxy-1-methylethyl 5-chloroquinolin-8-oxyacetate

Ausbeute 72.4%

Lösungsmittel

methylene chloride

dimethylformamide

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare then added
2. 2
   Sonstigethe precipitate which has separated out
3. 3
   Filtrationis filtered off with suction
4. 4
   Waschenrinsed with 50 ml of methylene chloride
5. 5
   WaschenThe filtrate is washed with 100 ml of 0.5 N HCl, with 100 ml of potassium bicarbonate solution and with 3 portions of in each case 50 ml of water
6. 6
   TrocknenThe organic phase is dried over magnesium sulfate
7. 7
   SonstigeThe residue is recrystallized from n-heptane

Vorschrift

5.0 g (0.021 mol) of 5-chloroquinolin-8-oxyacetic acid and 2.44 g (0.021 mol) of 2-allyloxy-1-methylethanol are suspended in a mixture of 40 ml of methylene chloride and 40 ml of dimethylformamide and the suspension is cooled to 0° C. 4.78 g (0.023 mol) of dicyclohexylcarbodiimide, dissolved in 10 ml of methylene chloride, are added dropwise at this temperature, and 200 mg of 3-(N,N-dimethylamino)-pyridine are then added. The mixture is stirred at room temperature for 15 hours and the precipitate which has separated out is filtered off with suction and rinsed with 50 ml of methylene chloride. The filtrate is washed with 100 ml of 0.5 N HCl, with 100 ml of potassium bicarbonate solution and with 3 portions of in each case 50 ml of water. The organic phase is dried over magnesium sulfate and the solvent is stripped off in vacuo. The residue is recrystallized from n-heptane. 5.1 g (72.4% of theory) of 2-allyloxy-1-methylethyl 5-chloroquinolin-8-oxyacetate of melting point 59° C. are obtained in this manner.

Quelle