1,3-Dihydro-3,3-dimethyl-2H-indol-2-one Chemical Properties

Melting point:

154.3°C

Boiling point:

287.51°C (rough estimate)

Density 

1.078

refractive index 

1.5200 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

14.85±0.40(Predicted)

color 

Yellow

InChI

InChI=1S/C10H11NO/c1-10(2)7-5-3-4-6-8(7)11-9(10)12/h3-6H,1-2H3,(H,11,12)

InChIKey

KEZHRKOVLKUYCQ-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C(C)(C)C1=O

Safety Information

HS Code 

2933998090

1,3-Dihydro-3,3-dimethyl-2H-indol-2-one Usage And Synthesis

Uses

3,3-Dimethyloxindole is used as an isoquinolin-1-amine based ROCK-I inhibitors. Also used in the preparation of a P2Y1 antagonists as effacacious antiplatelet agents.

Synthesis Reference(s)

Tetrahedron, 48, p. 7297, 1992 DOI: 10.1016/S0040-4020(01)88268-5

Synthesis

To a solution of 2-indolone (5 g, 37.55 mmol) and lithium chloride (5.6 g, 131.4 mmol) in tetrahydrofuran (100 mL) was added n-butyllithium (2.5 M, 30 mL) dropwise at -78 °C. The reaction mixture was stirred at -78 °C for 20 min, followed by the addition of iodomethane (4.8 mL, 75.1 mmol). The reaction system was warmed to 25 °C and stirred overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (100 mL) and extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed sequentially with water (100 mL) and saturated saline (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 8:1, v/v) to afford 1,2-dihydro-3,3-dimethyl-2-oxo-3H-indole as a white solid (2.92 g, 48.3% yield). Mass spectrum (ESI, positive ion mode) m/z: 162 [M+H]+; NMR hydrogen spectrum (CDCl3) δ (ppm): 9.23 (s, 1H), 7.21-7.18 (m, 2H), 7.04 (t, 1H), 6.96 (d, 1H), 1.41 (s, 6H).

References

[1] Patent: WO2014/89324, 2014, A1. Location in patent: Paragraph 0202
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4929 - 4931
[3] Patent: US2007/72897, 2007, A1. Location in patent: Page/Page column 66
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 419 - 430
[5] ChemMedChem, 2016, vol. 11, # 5, p. 497 - 508

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