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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at -18℃; for 1h;
Step 2.1 : 2-Amino-5-bromo-isonicotinonitrile.A solution of <strong>[42182-27-4]2-amino-isonicotinonitrile</strong> (10.0 g, 83.9 mmol) in DMF (20 mL) was cooled to -18°C (ice / MeOH bath), treated with NBS (16.5 g, 92.3 mmol), and stirred at -18°C for 1 h. The reaction mixture was diluted in AcOEt (500 mL) and washed with water {200 mL). The aqueous phase was separated and extracted with AcOEt (2 x 500 ml). The combined organic fractions were dried over Na.sum.SO/t, filtered and evaporated. The residue was purified by Combi-Flash Companion.(TM). (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane / DCM 1 :1] / TBME 98:2 --> 6:4) to yield the title compound (13.0 g, 65.6 mmol, 78percent) as a pale yellow solid. MS: 199 [M+1]+ ; HPLC: \\et = 1.13; TLC: RF 0.39 (hexane / DCM / TBME 1 :1 :2).
60%
With dihydrogen peroxide; 1-butylpyridinium bromide; toluene-4-sulfonic acid; In 1,2-dimethoxyethane; at 80℃; for 24h;Schlenk technique; Inert atmosphere; Green chemistry;
General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80°C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.
With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; for 3h;Heating / reflux;
A stirred mixture of commercially available 2-amino-4-cyano-pyridine [CAS-No. 42182-27-4] (1.0 g, 8.39 mmol), hydroxylamine hydrochloride (1.17 g, 16.8 mmol) and sodium carbonate (0.89 g, 8.39 mol) in water (8 mL) and ethanol (16 mL) was heated under reflux conditions for 3 h. The reaction mixture was evaporated, water (10 mL) was added and the mixture stirred at room temperature for 1 h. The precipitate was collected by filtration to yield the title compound (0.87 g, 68percent) as an off-white solid. MS (EI) 152.0 [(M)+]; mp 188° C.
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