* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Chemische Berichte, 1880, vol. 13, p. 963[2] Chemische Berichte, 1881, vol. 14, p. 417
2
[ 102170-56-9 ]
[ 175610-68-1 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 4, p. 391 - 392
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 4, p. 437 - 448
3
[ 102170-56-9 ]
[ 685109-10-8 ]
Yield
Reaction Conditions
Operation in experiment
49%
With acetic acid; sodium nitrite In water at 20℃; for 1 h; Cooling with ice
To a solution of 2-bromo-6-methyi-4-nitroaniline (14.1 g,61.0 mmol) in glacial acetic acid (162 mL) was added a solution of sodium nitrite (6.32 g, 91.Smmol) in water (14 mL) dropwise over 10 mm. During this time, the reaction solution was cooled in an ice bath to maintain an internal reaction temperature below 25 °C. The reaction was stirred at 20 °C for 1 hr. The reaction solution was concentrated in vaeuo, and the residue wastriturated with I : 1 methanoi:water, The resulting precipitate was collected by filtration, and dried in vaeuo at 80 °C for 6 hr to afford the title compound (10.4 g, 49percent) as a red solid. MS (ESI): mass calcd. for C71-L,BrN3O2 241.0. m/z found 242 [M±Hf, ‘H NMR (300 MHz, DMSO-d6) 15 8.84 (s. 1H), 8.53 (s, 1H), 8.37 (s, 11-i),
49%
With acetic acid; sodium nitrite In water at 0 - 20℃; for 12.17 h;
General procedure: To a 0 °C solution of 2-chloro-6-methyl-4-nitroaniline (15a)(0.9 g, 4.9 mmol) in glacial acetic acid (18 mL) was added a solutionof NaNO2 (0.40 g, 5.8 mmol) in 4 mL water dropwise over a periodof 10 min with stirring. The mixture was allowed to warm to roomtemperature and stirred for 12 h. The precipitate was removed byfiltration of the reaction mixture through a pad of Celite. The filtratewas poured into H2O (100 mL); the solid was collected by filtrationand purified by silica gel column chromatography (DCM/MeOH100:1 as eluent) to afford 16a as a light brown solid (0.50 g, 52percent).
Reference：
[1] Patent: WO2016/176460, 2016, A1, . Location in patent: Page/Page column 97
[2] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
With acetic acid; sodium nitrite; In water; at 20℃; for 1h;Cooling with ice;
To a solution of 2-bromo-6-methyi-4-nitroaniline (14.1 g,61.0 mmol) in glacial acetic acid (162 mL) was added a solution of sodium nitrite (6.32 g, 91.Smmol) in water (14 mL) dropwise over 10 mm. During this time, the reaction solution was cooled in an ice bath to maintain an internal reaction temperature below 25 C. The reaction was stirred at 20 C for 1 hr. The reaction solution was concentrated in vaeuo, and the residue wastriturated with I : 1 methanoi:water, The resulting precipitate was collected by filtration, and dried in vaeuo at 80 C for 6 hr to afford the title compound (10.4 g, 49%) as a red solid. MS (ESI): mass calcd. for C71-L,BrN3O2 241.0. m/z found 242 [M±Hf, ?H NMR (300 MHz, DMSO-d6) 15 8.84 (s. 1H), 8.53 (s, 1H), 8.37 (s, 11-i),
49%
With acetic acid; sodium nitrite; In water; at 0 - 20℃; for 12.17h;
General procedure: To a 0 C solution of 2-chloro-6-methyl-4-nitroaniline (15a)(0.9 g, 4.9 mmol) in glacial acetic acid (18 mL) was added a solutionof NaNO2 (0.40 g, 5.8 mmol) in 4 mL water dropwise over a periodof 10 min with stirring. The mixture was allowed to warm to roomtemperature and stirred for 12 h. The precipitate was removed byfiltration of the reaction mixture through a pad of Celite. The filtratewas poured into H2O (100 mL); the solid was collected by filtrationand purified by silica gel column chromatography (DCM/MeOH100:1 as eluent) to afford 16a as a light brown solid (0.50 g, 52%).
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