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With sulfuric acid; iodine; acetic acid; periodic acid In water at 80℃; for 6 h;
To a stirred solution of 6-methyl-pyridin-2-ylamine (30g, 278mmol, 1 eq) in acetic acid (167ml_) was added periodic acid (12.7g, 55.6mmol, 0.2eq) followed by addition of sulphuric acid (4.8ml_, 90.8mmol, 0.34eq), water (33ml_) and iodine (28.7g, 1 1 1 mmol, 0.4eq) at room temperature. Resulting reaction mixture was heated at 80°C for 6 hours. After complete consumption of starting material, reaction mixture was cooled and poured into sodium thiosulfate solution (200ml_), reddish oil was settled down at the bottom. Reaction mixture was decanted from reddish oil, and filtrate was basified with 50percent sodium hydroxide solution (100ml_), yellow colored solid was formed. Resulting solid was extracted with diethyl ether (2 x 200ml_) and dried over sodium sulfate. Organic layer was concentrated under reduced pressure to afford brown semi solid (60g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 15percent EtOAc in hexane to get title compound as faint brown solid (50g, 77percent). H NMR (400 MHz, CDCI3)8: 2.52 (s, 3H), 4.43(bs, 2H), 6.09 (d, J = 8.4 Hz, 1 H), 7.65 (d, J = 8.44 Hz, 1 H). LC-MS (m/z): 235.3 (M+H).
38%
With sulfuric acid; iodine; acetic acid In water
PREPARATION 2 2-amino-5-iodo-6-picoline A mixture of 2-amino-6-picoline (5.40 g), periodic acid (2.28 g), and iodine (5.00 g) is heated in a solution of acetic acid (30 mL), water (6 mL), and sulfuric acid (0.9 mL) at 80° C. for 3 h. The reaction is cooled to room temperature and poured into 100 mL 10percent aqueous sodium bisulfite. The aqueous solution is extracted with diethyl ether (3*100 mL). The combined organics are washed with 10percent NaOH, then dried over Na2SO4, filtered, and concentrated. Purification by chromatography (eluent EtOAc) affords a yellow liquid. The liquid is further dried on the vacuum pump where it crystallizes to afford 2-amino-5-iodo-6-picoline (4.48 g, 38percent). Physical characteristics are as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.60, 6.09, 6.05, 2.38.
7.5 g
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃;
(A) 5-iodo-6-methylpyridin-2-amine (0307) To a solution of 6-methylpyridin-2-amine (10 g, 0.092 mol) in DMF (50 mL) was added N-iodosuccinimide (15 g, 0.13 mol), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (200 mL), and the precipitated solid was collected by filtration and washed with ethyl acetate to give the title compound (7.5 g). MS: [M+H]+ 235.0
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