6,7-DIHYDRO-5H-1-PYRIDIN-5-ONE Chemical Properties

Melting point:

64-66 °C

Boiling point:

125 °C(Press: 9 Torr)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

3.47±0.20(Predicted)

Appearance

Gray to brown Solid

InChI

InChI=1S/C8H7NO/c10-8-4-3-7-6(8)2-1-5-9-7/h1-2,5H,3-4H2

InChIKey

LMEREVKJVWUGJI-UHFFFAOYSA-N

SMILES

C12CCC(=O)C1=CC=CN=2

Safety Information

HS Code 

2933399990

6,7-DIHYDRO-5H-1-PYRIDIN-5-ONE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 6,7-dihydrocyclopenta[b]pyridin-5-one using 2,3-cyclopentenopyridine as starting material was as follows: 0.883 mg of Mn(OTf)2 (0.5 mol%), 60 mg of 2,3-cyclopentenopyridine, 0.35 g of 65% aqueous TBHP and 2.5 mL of water were added sequentially to 25 mL of a round bottomed flask. The reaction system was stirred in air at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 × 5 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether and ethyl acetate (5:1, v/v) as eluent to afford 60.5 mg of 6,7-dihydro-5H-cyclopentadieno[b]pyridin-5-one as a light yellow solid in 91% yield.

References

[1] Patent: CN105669548, 2016, A. Location in patent: Paragraph 0027; 0028
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4078 - 4082
[3] Angew. Chem., 2018, vol. 130, # 15, p. 4142 - 4146,5
[4] Chinese Journal of Catalysis, 2016, vol. 37, # 8, p. 1216 - 1221
[5] Organic Letters, 2018, vol. 20, # 7, p. 1987 - 1990

6,7-DIHYDRO-5H-1-PYRIDIN-5-ONE(28566-14-5)Related Product Information

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