4-AMINOISOINDOLIN-1-ONE Chemical Properties

Melting point:

225-230°

Boiling point:

489.8±45.0 °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

Light yellow to yellow Solid

InChI

InChI=1S/C8H8N2O/c9-7-3-1-2-5-6(7)4-10-8(5)11/h1-3H,4,9H2,(H,10,11)

InChIKey

GZRGLZWHIFBBLS-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(N)=CC=C2)CN1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

4-AMINOISOINDOLIN-1-ONE Usage And Synthesis

Uses

4-Aminoisoindolin-1-one is s a reactant that has been used in the synthesis of 4-(N-acyl)-2,3-dihydro-1H-isoindol-1-ones as potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1).

Synthesis

General procedure for the synthesis of 4-aminoisoindolin-1-one from 4-nitro-isoindolin-1-one: A mixture of 4-nitro-2,3-dihydro-1H-isoindolin-1-one (20 g), ammonium formate (35 g), and 7.5% Pd/C (0.6 g) in methanol (60 ml) was stirred for 2 hr at 35° C. The reaction was completed by filtration to remove the catalyst. After completion of the reaction, the Pd/C catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was recrystallized by water to give 15.3 g of light yellow solid product in 92% yield. Melting point: 195.6-197°C. 1H-NMR (300 MHz, DMSO-d6) δ: 4.31 (s, 2H), 6.76 (d, 1H), 7.14 (t, 1H), 6.86 (d, 1H), 5.30 (s, 2H), 8.26 (s, 1H). 1H-NMR (300 MHz, DMSO-d6/D2O 1H-NMR (300MHz, DMSO-d6/D2O) δ: 4.14 (s, 2H), 6.79 (d, 1H), 6.93 (d, 1H), 7.16 (t, 1H) FAB (M + 1): 149 Elemental analysis: theoretical value (%): C 64.85, H 5.44, N 18.91; measured value (%): C 64.96, H 5.61, N 19.02. HPLC test conditions: Chromatography Column: Phenomenex Luna 5u C18 (250 mm×4.6 mm); Flow rate: 1.0 ml/min; Detection wavelength: 230 nm; Mobile phase: Acetonitrile/0.1% Phosphate=15/85 or Acetonitrile/0.01M Ammonium Acetate=10/90; Retention time of the target product: 3.580 min; 4.790 min. Purity of target product: 99.66%.

References

[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 248 - 253
[2] Angew. Chem., 2017, vol. 129, # 1, p. 254 - 259,6
[3] Patent: WO2010/139266, 2010, A1. Location in patent: Page/Page column 38-39
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[5] Patent: US2002/95044, 2002, A1

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