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ChemicalBook--->CAS DataBase List--->69047-36-5

69047-36-5

69047-36-5 Structure

69047-36-5 Structure
IdentificationBack Directory
[Name]

1H-Indole-7-carboxaldehyde, 1-methyl- (9CI)
[CAS]

69047-36-5
[Synonyms]

1-METHYL-1H-INDOLE-7-CARBALDEHYDE
1-Methyl-1H-indole-7-carboxaldehyde
1H-Indole-7-carboxaldehyde, 1-Methyl-
1H-Indole-7-carboxaldehyde, 1-methyl- (9CI)
[Molecular Formula]

C10H9NO
[MOL File]

69047-36-5.mol
[Molecular Weight]

159.185
Chemical PropertiesBack Directory
[Melting point ]

82-84 °C
[Boiling point ]

318.7±15.0 °C(Predicted)
[density ]

1.10±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[Appearance]

White to off-white Solid
[CAS DataBase Reference]

69047-36-5
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

1H-Indole-7-carboxaldehyde, 1-methyl- (9CI)(69047-36-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

Indole-7-carboxaldehyde

1074-88-0

Iodomethane

74-88-4

1H-Indole-7-carboxaldehyde, 1-methyl- (9CI)

69047-36-5

GENERAL STEPS: Example I Synthesis of 1-methyl-1H-indole-7-carbaldehyde 20 g of 1H-indole-7-carboxaldehyde was dissolved in 160 ml of N,N-dimethylformamide (DMF) and 15.5 g of potassium tert-butoxide was added in batches under argon protection. After addition, the reaction mixture was stirred for 20 min, followed by slow dropwise addition of 8.7 ml of iodomethane. After the dropwise addition, the reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. All organic phases were combined and washed with saturated aqueous sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was recrystallized from water. The resulting solid was filtered by pumping and dried under vacuum. Yield: 20 g (91% yield). Mass spectrum (ESI+): m/z = 160 [M + H]+.

[References]

[1] Patent: US2011/269737, 2011, A1. Location in patent: Page/Page column 40
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079
[3] Patent: WO2004/52890, 2004, A1. Location in patent: Page 92-93
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5115 - 5129
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