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CAS No. : | 53636-70-7 | MDL No. : | MFCD00075289 |
Formula : | C8H7NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PHQBKLKZIXCRIX-UHFFFAOYSA-N |
M.W : | 181.15 | Pubchem ID : | 542567 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
69% | With Iron(III) nitrate nonahydrate; tetrabutylammomium bromide; nitric acid; In water; at 90℃; for 16h; | (1) Put 30 g of water into the reaction kettle, turn on the stirring, and sequentially add Fe (NO3) 3.9H2O 0.06 g, 58% nitric acid 15 g, tetrabutylamine bromide 0.03 g, and 2-methylquinoline 2.75 g ;(2) When the reaction temperature reaches 90 C, 20g of oxone is added in batches, and the reaction is incubated for 16h after the addition;(3) After the reaction is completed, reduce the temperature to -10 to 10 C, slowly add concentrated ammonia water dropwise under stirring to adjust the pH value to 0.6 to 1, and then continue stirring for 2h, suction filtration, and drying to obtain 6-methyl-2,3- Pyridine dicarboxylic acid, the filtrate can be used for further product recovery, yield 69%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 0C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D16 (8.2 g, 50.3 mmol, 91 % yield) as a slightly brown solid. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H). |
74% | With pyridine; acetic acid; In 1,2-dimethoxyethane; at 20℃; for 2h; | Preparation 2 2-Methyl-furo[3,4-b]pyridine-5,7-dione A solution of 6-methyl-1,2-pyridine dicarboxylic acid (25 g, 138 mmol) and acetic acid (42 mL, 733 mmol) in DME (150 mL) is treated with pyridine (22 mL, 272 mmol) and stirred at room temperature for 2 h. The pale yellow solution is diluted with ether (250 mL) and then hexane (1250 mL) is added slowly. A white precipitate is formed. The solution is cooled to 0 C. for 30 min and the white solid is collected by filtration. The solid is washed with hexane and dried to give the title compound as a white solid (16.7 g, 74%). |
With acetic anhydride; In dichloromethane; | EXAMPLE 14 A mixture of <strong>[53636-70-7]6-methylpyridine-2,3-dicarboxylic acid</strong> (19.75 g) and acetic anhydride (51 ml) was stirred and heated in an oil bath (bath temperature 110 C.) for 5 hours. The solvent was removed in vacuo and a 2:1 mixture of dichloromethane and ether was added, giving a dark brown solid. A solution of this solid in dichloromethane was passed through a pad of silica gel, eluding with dichloromethane, and the solvent was then evaporated to give partially purified <strong>[53636-70-7]6-methylpyridine-2,3-dicarboxylic acid</strong> anhydride (12.1 g). |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C. under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D40 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1H), 7.82 (d, 1H), 2.73 (s, 3H). | |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | in a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 0C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D55 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H). | |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | Description 23: 2-methylfuro[3,4-b]pyridine-5,7-dione (D23); In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 0C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D23 (8.2 g) as a slightly brown solid.1H NMR (400 MHz, DMSO-J6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H). | |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D34 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H). | |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D60 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H). | |
With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | In a 100 ml round-bottomed flask <strong>[53636-70-7]6-methyl-2,3-pyridinedicarboxylic acid</strong> (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 0C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D32 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H) | |
4.97 g | With acetic anhydride; at 100℃; for 5h;Inert atmosphere; | <strong>[53636-70-7]6-methylpyridine-2,3-dicarboxylic acid</strong> (5.50 g, 30.36 mmol) was dissolved in Acetic anhydride (14.3 ml_) and the mixture heated at 100 C under nitrogen for 5 hours. Volatiles were removed under vacuum to give 2-methyl-5H,7H-furo[3,4-b]pyridine-5,7- dione (Int. a, 4.97 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.7% | hydrogenchloride; In isopropyl alcohol; for 16h;pH 2.0;Heating / reflux; | 6-methyl-2, 3-PYRIDINEDICARBOXYLIC acid (5.1 g, 0.03 mol) was dissolved in MEOH (80 ml) and the pH was adjusted to 2 with HCI/isopropanol 6N. This mixture was heated at reflux for 16 hrs. After evaporating MEOH, the residue was co-evaporated two times with toluene and dried in a vacuum oven to get a yellow solid (5. 81g, 98.7%). MS: [M+H] +=210 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With pyridine; In 1,2-dimethoxyethane; at 20℃; for 1.5h; | EXAMPLES Example 1 N-(2-Amino-6-methylpyridin-3-ylmethel .-N- {2-[2-[(2-amino-6-methyl-pyndin-3- ylmethyl fbrmylammo]-l- (2-hydroxyethyl)-propenyldisulfanyl]-4-hydroxy-l- methylbut-1-enyl} formamide (III-13) [0115] a) 2-Methylfuro[3,4-b]pyridine-5,7-dione. To a solution of 6-methyl-2,3- pyridinedicarboxylic acid (41*5g, 229mmol) and acetic anhydride (70mL) in 250mL of 1,2-dimethoxyethane was added pyridine (37mL). The reaction mixture was stirred at room temperature for 90 min. The solution was diluted with ether (50mL) and hexane (150mL) was added until the solution became cloudy. The solution was stirred in an ice-water bath until a white precipitate formed. The precipitated solid was collected by filtration and dried under vacuum overnight to give 20.7g (55%) of the title compound as a white crystalline solid. 1H NMR (CDCl3) 8 2. 85 (s, 3H), 7. 68 (d, 1H), 8.25 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | 6-Methyl-2,3-pyridinedicarboxylic acid (10.0 g, 0. [055] mol) and [AC20] [(50] mL) were heated at [120 C] for 4 h, cooled, and concentrated to a brown oil. Isopropanol was added to the brown oil and the solution heated at [80 C] overnight. The volatiles were removed in vacuo and the residue gave, after washing with diethyl ether, 6- [METHYLPYRIDINE-2,] 3-dicarboxylic acid 2-isopropyl ester as a straw-coloured solid (8.8 g, [71%).-IH] NMR [(CDC13)] : 5 8.24 (d, [J=8.] 2, [1] H), 7.34 (d, [J=8.] 2,1 H), 5.34 [(SEP,] [J=6.] 2, [1 H),] 2.68 (s, 3 H), 1.39 (d, [J=6.] 2, [6 H).] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.5% | With sodium hydroxide In methanol at 80℃; for 74h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In N,N-dimethyl-formamide at 90℃; for 70h; | 2.2. Synthesis of metal complexes For metal complex 1 : Zn(CH 3 COO) 2 ·2H 2 O (0.5 mmol), 6-Me- 2,3-pydc (0.5 mmol) were added in a mixture solution of DMF (2 mL) and H 2 O (10 mL) and carefully putted in a reactor. The synthe- sis method of metal complex 1 is shown in Scheme 1 (a). After 70 h of reaction at 90 °C, slowly cool to 25 °C, transparent bulk crys- tals were formed, filter, and put it in a 50 °C vacuum dried oven for 12 h to obtain 0.0599 g [Zn(6-Me-2,3-pydc)(H 2 O) 2 ·2H 2 O] n (namely complex 1 ). The yield of 53% based on the Zn(CH 3 COO) 2 ·H 2 O. Anal. Calc. (%) for C 8 H 13 NO 8 Zn (%): C, 30.35; H, 4.14; N, 4.42. Found (%): C, 30.87; H, 3.76; N, 4.82. The synthesis method of metal complex 2 is shown in Scheme 1 (b) and the synthesis process consistent with metal complex 1 : the raw materials were NiSO 4 ·6H 2 O (0.5 mmol), 5-Br-2,3-pydc (0.5 mmol), 1,10-phen (0.5 mmol), NaOH (0.5 mmol), the mixture solution of DMF (2 mL) and H 2 O (13 mL). The reaction temperature was 150 °C and the reaction time was 65 h. Obtained 0.0467 g purple bulk crystals with the formula [Ni(5-Br- 2,3-pydc) (1,10-phen) 2 ·9H 2 O] n (namely complex 2 ). Anal. Calc. (%) for C 31 H 36 BrN 5 O 13 Ni (%): C, 45.12; H, 4.40; N, 8.49. Found (%): C, 45.31; H, 4.45; N, 8.37. |
Tags: 53636-70-7 synthesis path| 53636-70-7 SDS| 53636-70-7 COA| 53636-70-7 purity| 53636-70-7 application| 53636-70-7 NMR| 53636-70-7 COA| 53636-70-7 structure
[ 53636-65-0 ]
5-Methylpyridine-2,3-dicarboxylic acid
Similarity: 0.96
[ 875256-15-8 ]
3-(Hydroxymethyl)picolinic acid
Similarity: 0.94
[ 81113-14-6 ]
2-(Hydroxymethyl)nicotinic acid
Similarity: 0.93
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