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54189-82-1

54189-82-1 Structure

54189-82-1 Structure
IdentificationBack Directory
[Name]

6-CHLORO-N-METHYL-NICOTINAMIDE
[CAS]

54189-82-1
[Synonyms]

6-CHLORO-N-METHYL-NICOTINAMIDE
6-chloro-nicotinic acid N-MethylaMide
3-Pyridinecarboxamide, 6-chloro-N-methyl-
[Molecular Formula]

C7H7ClN2O
[MDL Number]

MFCD08460991
[MOL File]

54189-82-1.mol
[Molecular Weight]

170.6
Chemical PropertiesBack Directory
[Melting point ]

152.8-153.4 °C(Solv: dichloromethane (75-09-2))
[Boiling point ]

347.6±27.0 °C(Predicted)
[density ]

1.264±0.06 g/cm3(Predicted)
[storage temp. ]

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

13.85±0.46(Predicted)
[Appearance]

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

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

6-CHLORO-N-METHYL-NICOTINAMIDE(54189-82-1)1HNMR
6-CHLORO-N-METHYL-NICOTINAMIDE(54189-82-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

6-CHLORONICOTINOYL CHLORIDE

58757-38-3

Methylamine

74-89-5

6-CHLORO-N-METHYL-NICOTINAMIDE

54189-82-1

a) Preparation of 6-chloro-N-methylnicotinamide: 6-chloro-3-pyridinecarbonyl chloride (5.65 g, 32.1 mmol) was dissolved in tetrahydrofuran (64 mL), and triethylamine (5.59 mL, 40.1 mmol) and tetrahydrofuran solution of methylamine (20.1 mL, 40.1 mmol) were added sequentially, and the reaction was carried out under the condition of ice bath. After addition, the ice bath was withdrawn and the reaction was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the resulting residue was purified by recrystallization (ethyl acetate/hexane) to afford 6-chloro-N-methyl-nicotinamide (5.06 g, 92% yield) as light brown crystals.1H-NMR (CDCl3) δ: 3.05 (3H, d, J = 4.6 Hz), 6.14 (1H, brs), 7.42 (1H, d, J = 8.3 Hz), 8.09 (1H, dd, J = 2.4, 8.3 Hz), 8.72 (1H, d, J = 2.4 Hz).

[References]

[1] Patent: US2010/280013, 2010, A1. Location in patent: Page/Page column 13
[2] Patent: US2010/48610, 2010, A1. Location in patent: Page/Page column 22
[3] Patent: US2009/69300, 2009, A1. Location in patent: Page/Page column 28
[4] Patent: WO2005/97778, 2005, A1. Location in patent: Page/Page column 26
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