2H-INDOL-2-ONE, 6-AMINO-1,3-DIHYDRO- Chemical Properties

Melting point:

200 °C (decomp)

Boiling point:

394.3±42.0 °C(Predicted)

Density 

1.307±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.24±0.20(Predicted)

Appearance

Brown to black Solid

2H-INDOL-2-ONE, 6-AMINO-1,3-DIHYDRO- Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-aminoindolones from 2,4-dinitrophenylacetic acid: 2,4-dinitrophenylacetic acid (10 g, 44 mmol) was dissolved in ethanol (200 mL) and purged with nitrogen. 10% Pd/C catalyst (400 mg) was added and the reaction was hydrogenated at 45 psi hydrogen pressure for 2 hours. Upon completion of the reaction, the mixture was transferred to a round bottom flask, p-toluenesulfonic acid (150 mg) was added, and heated to reflux overnight. The reaction mixture was filtered through diatomaceous earth to remove the catalyst and the filtrate was subsequently concentrated. The product precipitated as brown crystals and 4.68 g (72% yield) was obtained by filtration. The product was characterized by 1H NMR (DMSO-d6, 400 MHz): δ 3.20 (s, 2H), 4.97 (br s, 2H), 6.07 (m, 2H), 6.76 (d, J = 8.7 Hz, 1H), 10.05 (s, 1H); HPLC retention time: 2.123 min; LRMS (M+) 148.7.

References

[1] Patent: US2005/256125, 2005, A1. Location in patent: Page/Page column 29
[2] Patent: WO2009/79767, 2009, A1. Location in patent: Page/Page column 87
[3] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10939 - 10954
[4] ChemMedChem, 2012, vol. 7, # 5, p. 777 - 791
[5] Chemische Berichte, 1881, vol. 14, p. 830

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