5H-Cyclopenta[c]pyridin-5-one,6,7-dihydro-(9CI) Chemical Properties

Boiling point:

267.4±9.0 °C(Predicted)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

pka

3.56±0.20(Predicted)

Appearance

Brown to black Solid

Safety Information

HazardClass 

IRRITANT

5H-Cyclopenta[c]pyridin-5-one,6,7-dihydro-(9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of 6,7-dihydro-5H-cyclopentadieno[c]pyridin-5-one from methyl 3-(3-ethoxy-3-oxopropyl)isonicotinate: to a tetrahydrofuran (THF, 5.0 mL) solution of methyl 3-(3-ethoxy-3-oxopropyl)isonicotinate (300 mg, 1.26 mmol) was added potassium 2-methylpropan-2-ol ( 0.28 g, 2.52 mmol). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the solvent was evaporated to dryness. Concentrated hydrochloric acid (5 mL) was added to the residue and the reaction mixture was stirred at 100 °C for 2 hours. After continuing to stir at 100 °C for 16 h, saturated aqueous sodium bicarbonate (40 mL) and ethyl acetate (EtOAc, 50 mL) were added to the reaction vessel, and the resulting two-phase mixture was transferred to a partition funnel. The organic and aqueous layers were separated and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by fast column chromatography using isocratic elution conditions of ethyl acetate (35%) and hexane (65%) to afford 6,7-dihydro-5H-cyclopenta[c]pyridin-5-one (0.03 g, 0.23 mmol) as a gray oil.

References

[1] Patent: WO2018/26371, 2018, A1. Location in patent: Paragraph 0132; 0134; 0283

5H-Cyclopenta[c]pyridin-5-one,6,7-dihydro-(9CI)(350847-80-2)Related Product Information

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