| Identification | More | [Name]
5-Aminooxindole | [CAS]
20876-36-2 | [Synonyms]
2H-INDOL-2-ONE, 5-AMINO-1,3-DIHYDRO-
5-AMINO-1,3-DIHYDRO-INDOL-2-ONE
5-AMINO-2-OXINDOLE
5-AMINOOXINDOLE
CHEMBRDG-BB 4006397
TIMTEC-BB SBB010120
5-Amino-1,3-dihydro-2H-indol-2-one
5-Aminooxindole, 5-Amino-2-oxoindoline | [Molecular Formula]
C8H8N2O | [MDL Number]
MFCD02179603 | [Molecular Weight]
148.16 | [MOL File]
20876-36-2.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
13.91±0.20(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933790090 |
| Hazard Information | Back Directory | [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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