5-Aminooxindole Chemical Properties

Melting point:

182-186°C

Boiling point:

416.8±45.0 °C(Predicted)

Density 

1.307±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

13.91±0.20(Predicted)

form 

Solid

color 

Dark Green to Brown

InChI

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

InChIKey

JPUYXUBUJJDJNL-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(N)C=C2)CC1=O

CAS DataBase Reference

20876-36-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933790090

5-Aminooxindole Usage And Synthesis

Uses

5-Amino-2-indolinone is useful in the synthesis of anticancer drugs, Cyclin dependent kinase inhibitors and spleen tyrosine kinase (Syk) inhibitors.

Synthesis

General procedure for the synthesis of 5-amino-dihydroindol-2-one from 5-nitroindol-2-one: 5-nitrodihydroindol-2-one (5 g, 1 equiv.) was suspended in ethanol (50 mL), activated charcoal (1 g) and ferric chloride (1 g) were added. The reaction mixture was heated to 78 °C and stirred continuously for 10 minutes. Subsequently, 80% aqueous hydrazine hydrate (8 eq.) was slowly added dropwise to the reaction system over 5 minutes. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 78°C for 8-10 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered to remove the activated carbon residue. The filtrate was concentrated in vacuum to give the crude product, which was purified by recrystallization with ethanol (about 15 mL) to give the final 5-amino dihydroindol-2-one as a light yellow solid in 91.9% yield.

References

[1] Patent: US2004/39019, 2004, A1. Location in patent: Page/Page column 6
[2] Patent: US6268391, 2001, B1
[3] Journal of Antibiotics, 2018, vol. 71, # 10, p. 887 - 897
[4] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 274 - 288
[5] Patent: WO2016/198597, 2016, A1. Location in patent: Page/Page column 18; 19

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