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ChemicalBook--->CAS DataBase List--->22246-66-8

22246-66-8

22246-66-8 Structure

22246-66-8 Structure
IdentificationBack Directory
[Name]

5-METHOXY-2,3-DIHYDRO-ISOINDOL-1-ONE
[CAS]

22246-66-8
[Synonyms]

5-methoxyisoindolin-1-one
5-METHOXY-2,3-DIHYDRO-ISOINDOL-1-ONE
2,3-Dihydro-6-Methoxy-1H-isoindol-1-on
2,3-Dihydro-5-methoxy-1H-Isoindol-1-one
5-Methoxy-2,3-dihydro-1H-isoindol-1-one
1H-Isoindol-1-one, 2,3-dihydro-5-Methoxy-
2,2':6',2''-Terpyridine,4,4',7''-trimethyl-
[Molecular Formula]

C9H9NO2
[MDL Number]

MFCD08437636
[MOL File]

22246-66-8.mol
[Molecular Weight]

163.17
Chemical PropertiesBack Directory
[Melting point ]

160-161℃ (acetonitrile ethyl ether )
[Boiling point ]

439.2±45.0 °C(Predicted)
[density ]

1.208±0.06 g/cm3 (20 ºC 760 Torr)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

14.37±0.20(Predicted)
[Appearance]

White to light brown Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H315-H335-H302
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

5-METHOXY-2,3-DIHYDRO-ISOINDOL-1-ONE(22246-66-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-BROMOMETHYL-5-METHOXY-BENZOIC ACID METHYL ESTER

788081-99-2

5-METHOXY-2,3-DIHYDRO-ISOINDOL-1-ONE

22246-66-8

Methyl 2-bromomethyl-5-methoxybenzoate (75, 5.0 g, 19.3 mmol) was used as raw material and dissolved in methanol in a pressure flask. To this solution was added ammonia/methanol solution (2M, 30 ml). The reaction mixture was stirred at 125°C for 2 hours. After completion of the reaction, the solvent and excess ammonia were removed by distillation under reduced pressure. The resulting residue was ground with hexane/ethyl acetate (1:2 v/v). The solid product was vacuum filtered and dried in air for 2 h to afford 5-methoxy-2,3-dihydroisoindol-1-one (2.51 g, 65% yield) as a light yellow solid. The filtrate was concentrated and purified by silica gel column chromatography (eluent ratio hexane/ethyl acetate/methanol 3:1:0.5) to give an additional 270 mg of the target compound. The overall yield of the combined product was 86%. Mass spectrum (electrospray ionization) m/z 164.1.

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 222 - 227
[2] Patent: WO2006/138549, 2006, A1. Location in patent: Page/Page column 73
[3] Patent: WO2009/14637, 2009, A2. Location in patent: Page/Page column 70-71
[4] Patent: WO2010/54279, 2010, A1. Location in patent: Page/Page column 100-101
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7283 - 7287
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