2-[(2-Chloro-4-nitrophenoxy)methyl]pyridine Chemical Properties

storage temp. 

Inert atmosphere,Room Temperature

Appearance

Light brown to brown Powder

2-[(2-Chloro-4-nitrophenoxy)methyl]pyridine Usage And Synthesis

Uses

3-Chloro-4-(2-pyridylmethyloxy)nitrobenzene was used to synthesize aniline ''headgroups'' and incorporat them into an alkynyl thienopyrimidine series of EGFR and ErbB-?2 inhibitors.

Synthesis

General procedure for the synthesis of 2-((2-chloro-4-nitrophenoxy)methyl)pyridine from 2-chloro-4-nitrophenol and 2-chloromethylpyridine hydrochloride: 2-chloromethylpyridine hydrochloride (16.4 g, 0.1 mol) and potassium carbonate (K2CO3, 27.6 g, 0.2 mol) were suspended in N,N-dimethylformamide (DMF, 100 mL). stirred for 30 min at room temperature. Subsequently, 2-chloro-4-nitrophenol (17.4 g, 0.1 mol) and potassium iodide (KI, 0.83 g, 5 mol%) were added, and the reaction mixture was stirred for 12 hours at 60 °C. After completion of the reaction, the reaction mixture was diluted with water (400 mL), the resulting solid was collected by filtration, washed with water and dried to afford 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (26 g, 98% yield) as a white solid. The melting point of the product was 149.2-149.9 °C; mass spectra (MS-EI) m/z: 92, 229, 263 (M+).

References

[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3090 - 3104
[2] Patent: US2016/214964, 2016, A1. Location in patent: Paragraph 0138
[3] Patent: WO2005/10008, 2005, A1. Location in patent: Page/Page column 114-115
[4] Patent: WO2006/23843, 2006, A2. Location in patent: Page/Page column 64
[5] Patent: US2010/298297, 2010, A1. Location in patent: Page/Page column 14

2-[(2-Chloro-4-nitrophenoxy)methyl]pyridine(179687-79-7)Related Product Information

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