Diethyl Ether → Furo[2,3-c]isoquinolin-5(4H)-one

Temperatur

0 °C

Thionyl chloride (1 ml) was added to a suspension of 3-phenyl-2-furancarboxylic acid (300 mg, 1.46 mmol) in 10 ml of dry benzene and the mixture was refluxed for 2 hours. The solvent and the excess of thionyl chloride were removed under reduced pressure, the residue was taken up using 10 ml of dry THF and cooled to 0° C. Sodium azide (1.5 mmol) dissolved in the minimal amount of water was quickly added and the resulting solution was stirred for 1 hour at room temperature. After pouring into 100 ml of cracked ice/H2O and extraction with diethyl ether (4×100 ml), and the collected organic layers were dried over Na2SO4. The filtrate was gently evaporated under reduced pressure, the residue was dissolved in 10 ml of o-dichlorobenzene, and the resulting mixture was refluxed for 5-10 hours. The mixture was then cooled, and directly submitted to the flash chromatography, elution with dichloromethane/methanol (99/1) afforded to the title compound. Yield: 68%.

1. temperaturethe mixture was refluxed for 2 hours
2. customThe solvent and the excess of thionyl chloride were removed under reduced pressure
3. additionwas quickly added
4. dry with materialthe collected organic layers were dried over Na2SO4
5. customThe filtrate was gently evaporated under reduced pressure
6. dissolutionthe residue was dissolved in 10 ml of o-dichlorobenzene
7. temperaturethe resulting mixture was refluxed for 5-10 hours
8. temperatureThe mixture was then cooled
9. washdirectly submitted to the flash chromatography, elution with dichloromethane/methanol (99/1)

ORD-Eintrag

ord-833ade0696ae4240bb80c85ad20aaded

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08633215B2