Reaktion #220016

Reaktionsgleichung

product

Ethyl 6-benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate, hydrochloride

1-chloroethyl chloroformate

→

title compound

Ethyl 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate, hydrochloride salt

Lösungsmittel

methanol

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was warmed
2. 2
   Temperaturat reflux temperature overnight
3. 3
   EinengenThe reaction was concentrated under reduced pressure
4. 4
   Sonstigeto afford a yellow oil, which
5. 5
   Temperaturcooled to room temperature
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.ADDITIONTo the yellow solid was added diisopropyl ether
8. 8
   FiltrationThe pale yellow crystals were collected by filtration
9. 9
   Sonstigerecrystallized from ethanol

Vorschrift

A solution of the product from Step A above (0.095 mg, 0.287 mmol) in 10 mL of dichloromethane was treated with 1-chloroethyl chloroformate (0.050 g; 0.344 mmol), and the mixture was warmed at reflux temperature overnight. The reaction was concentrated under reduced pressure to afford a yellow oil, which was dissolved in 10 mL of methanol. The solution was heated at 40° C. for 2 h, cooled to room temperature and concentrated in vacuo. To the yellow solid was added diisopropyl ether. The pale yellow crystals were collected by filtration and recrystallized from ethanol to afford the title compound. LC/MS: 240.0 (M+1)

Quelle