Uses
2-Nitro-4''-chlorodiphenylamine is a reagent used in the synthesis of novel 4-phenoxyquinoline derivatives as c-Met kinase inhibitors. Intermediate for Clofazimine.
Preparation
4-Chlorobenzenamine and 1-Chloro-2-nitrobenzenecondensation
Synthesis
GENERAL METHOD: Suspend NaH (75 mmol) in DMF (60 mL) at 0°C and slowly add 4-chloroaniline (50 mmol). After stirring for 30 min at 0°C, a solution of 1-fluoro-2-nitrobenzene (60 mmol) in DMF (30 mL) was added dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was carefully poured into a stirred saturated NH4Cl solution (500 mL) and the precipitate was collected by filtration. The filter cake was washed with water and purified by recrystallization from methanol to give the target product N-(4-chlorophenyl)-2-nitroaniline (15h). The product was an orange solid with a yield of 72.3% and a melting point of 135.1-137.0 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.31 (s, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.53 (t, J = 7.6 Hz, 1H), 7.44 (d, J = 8.8 Hz, 2H), 7.34 (d, J = 8.8 Hz, 2H), 7.22 (d, J = 8.4 Hz, 1H), 6.93 (t, J = 7.6 Hz, 1H).MS (ESI) m/z (%): 247.2 [M-H]-.
Properties and Applications
Brilliant yellow
|
StandardVinegar fiber
|
Ironing Fastness
|
Light Fastness
|
Persperation Fastness
|
Washing Fastness
|
|
Fading
|
Stain
|
Fading
|
Stain
|
Fading
|
Stain
|
|
ISO
|
|
|
7
|
4
|
4
|
3
|
2
|
References
[1] Patent: CN106916069, 2017, A. Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021; 0022-0024
[2] Organic Process Research and Development, 2016, vol. 20, # 2, p. 452 - 464
[3] Molecules, 2012, vol. 17, # 4, p. 4545 - 4559
[4] Synlett, 2003, # 4, p. 564 - 566
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4475 - 4486
