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CAS No. : | 38116-61-9 | MDL No. : | MFCD00460503 |
Formula : | C7H7NO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | XRIHTJYXIHOBDQ-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 94960 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H319 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.1% | With sulfuric acid; at 0℃; for 21h;Reflux; | To a solution of <strong>[38116-61-9]2-hydroxy-6-methylnicotinic acid</strong> (10.0 g, 0.0653 mole) in methanol (100 mL), sulfuric acid (3.5 mL) was added drop wise at 0 C and the mixture was stirred for 21 h under reflux. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium bicarbonate solution under ice-cooling, and the mixture was extracted with 5 % methanol in chloroform (200 mL x 3). Organic layer was washed with brine solution (50 mL) and dried over Na2S04 and the solvent was concentrated under vacuum to afford the title compound. (0233) Yield: 7.0 g, 64.1%; 1H - NMR (DMSO- 6, 400 MHz) d ppm: 2.23 (s, 3H), 3.70 (s, 3H), 6.09 - 6.11 (d, J = 7.24 Hz, 1H), 7.98 - 8.00 (d, J = 7.36 Hz, 1H), 12.10 (s, 1H); Mass (m/z): 168.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38 g | With lithium aluminium tetrahydride; In tetrahydrofuran; at 70℃; for 1h;Inert atmosphere; | Reference Production Example 40 (0661) To a mixture of 50.0 g of <strong>[38116-61-9]2-hydroxy-6-methylnicotinic acid</strong> and 500 ml tetrahydrofuran, 18.6 g of lithium aluminum hydride was added in a nitrogen atmosphere at 70 C. for 1 hour. To the reaction mixture, 19 ml of water was added dropwise under ice cooling, followed by stirring at 0 C. for 1 hour. Furthermore, 16 ml of an aqueous 15% sodium oxide solution was added dropwise, followed by stirring at room temperature for 1 hour. The reaction mixture was filtered through Cerite and the filtrate was concentrated under reduced pressure to obtain 38.0 g of 2-hydroxy-3-hydroxymethyl-6-methylpyridine (hereinafter referred to as 40A). (0662) 1H-NMR (DMSO-D6) delta:6.82 (1H, d, J=6.8 Hz), 5.83 (1H, d, J=6.8 Hz), 4.25 (2H, s), 2.06 (3H, s). |
38 g | With lithium hydroxide; In tetrahydrofuran; at 70℃; for 1h;Inert atmosphere; | In the 70 C, to 50.0g of 2-hydroxy-6-methyl-nicotinic acid and 500 ml mixture of tetrahydrofuran, is added in the nitrogen atmosphere 18.6g alchlor hydrogenation of 1 hour. Frozen under the, dropping to the reaction mixture 19 ml of water, then in the 0 C stirring 1 hour. Furthermore, dropping 16 ml of a 15% sodium hydroxide aqueous solution, followed by stirring at room temperature 1 hour. The reaction mixture is filtered through a Cerite, and the filtrate concentrated under reduced pressure, to obtain 38.0g of 2-hydroxy-3-hydroxymethyl-6-methylpyridine (called below 40A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With hydrogenchloride; In 1,4-dioxane; for 16h;Reflux; | Preparation 211ethyl 2-hydroxy-6-methylpyridine-3-carboxylate To a solution of <strong>[38116-61-9]2-hydroxy-6-methylpyridine-3-carboxylic acid</strong> (2.0 g, 13.06 mmol) in ethanol (20 mL), was added HCI in dioxane (10 mL) dropwise and the reaction was refluxed for 16 hours. The reaction was concentrated in vacuo and basified with saturated aqueous sodiumbicarbonate solution. The mixture was extracted with ethyl acetate (twice), the organic layers were combined, washed with water, brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid (650 mg, 27%). 1H NMR (400 MHz, DMSO-d6): O ppm 1.24 (t, 3H), 2.22 (s, 3H), 4.16 (q, 2H), 6.08 (d, 1H), 7.97(d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 1; Step A:; A solution of NaOCl (1.2 L, of 5%) was cooled to 0 0C in ice bath. 2-hydroxy-6- methylpyrridine-3-carboxylic acid 1-1 (100 g, 0.65mol) was added in small portions. The resulting homogenous mixture was stirred at 0 0C for 1 hour and then at 1O0C for 5 hours. Another portion NaOCl(300 mL, of 5%) was added at O0C and the mixture was stirred at 100C overnight. The solution was acidified to pH = 1 with 12N HCl, and the resulting solid was filtered, washed with water, and oven dried to afford white solid product 1-2 (m/z (ES) (M+H)+= 188). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Diphenylphosphoryl azide (11.9 mL, 55 mmol) was added to a solution of <strong>[38116-61-9]2-hydroxy-6-methylpyridine-3-carboxylic acid</strong> (7.65 g, 50 mmol) and triethylamine (7.7 mL, 55 mmol) in dry dioxane (100 mL) and the resulting solution was heated to reflux. After 16 h more triethylamine (7.7 mL, 55 mmol) and benzyl alcohol (5.7 mL, 50 mmol) were added and the solution was refluxed for a further 24 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride (200 mL) and brine (100 mL), acidified to pH 1 with 10% HCl. The organic layer was washed with saturated NaHCO3 (2×100 mL), brine (100 mL), dried over Na2SO4 and filtered. After evaporating the solvent in vacuo, methanol (100 mL) and hexane (20 mL) were added to the residue, the solid was collected, washed with methanol (50 mL) and dried to give the title compound as a white solid (7.2 g, 56%). 1H-NMR (300 MHz, CDCl3) delta12.82 (s, 1H), 8.06 (d, J=7.0 Hz, 1H),7.69 (s, 1H), 7.42 (m, 5H), 6.09 (d, J=7.5 Hz, 1H), 5.22 (s, 2H), 2.32 (s, 3H). |