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[ CAS No. 65275-12-9 ] {[proInfo.proName]}

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Chemical Structure| 65275-12-9
Chemical Structure| 65275-12-9
Structure of 65275-12-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65275-12-9 ]

CAS No. :65275-12-9 MDL No. :MFCD11656385
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 167.16 Pubchem ID :-
Synonyms :

Safety of [ 65275-12-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65275-12-9 ]

* 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.

  • Downstream synthetic route of [ 65275-12-9 ]

[ 65275-12-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 41288-96-4 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 65275-12-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In N,N-dimethyl-formamide; at 50℃; under 760.051 Torr; Production Example 4-1: Ethyl 5-hydroxypyridine-2-carboxylate: Palladium acetate (267 mg), 1,1'-bis(diphenylphosphino)ferrocene (1.3 g) and triethylamine (3.2 mL) were added to an ethanol-DMF mixed solvent (1/1, 20 mL) of 6-chloropyridin-3-ol (1.5 g), and stirred overnight in a carbon monoxide atmosphere (1 atmospheric pressure) at 50C. Ethanol was evaporated off under reduced pressure from the reaction solution, water was added to the resulting residue, and extracted with chloroform/methanol (10/1). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate = 2/3) to obtain the entitled compound (500 mg).
  • 2
  • [ 15069-92-8 ]
  • [ 64-17-5 ]
  • [ 65275-12-9 ]
YieldReaction ConditionsOperation in experiment
55% To a stirred solution of 5-hydroxy-pyridine-2-carboxylic acid (1.25 g, 9.0 mmol) in ethanol (40 mL) was added concentrated sulfuric acid (3 mL, 56.3 mmol) and the resulting solution heated at reflux under an atmosphere of argon for 20 h. The solution was then cooled to O0C then sodium hydroxide (2 N, 55 mL) was added. Saturated aqueous sodium bicarbonate and 10% w/w citric acid solution were then added to bring the pH to 7 and the resulting solution concentrated to ~70 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL) and the combined organic extracts dried, filtered and concentrated to afford the title compound (829 mg, 55%) as an off white solid. MS: m/e = 168.3 [M+H]+.
With hydrogenchloride; In water; for 6h;Cooling with ice; Reflux; The compound XII (350.00g, 2 . 516 muM, 1 . 0eq.) dissolved in EtOH (3000 ml) in. Concentrated HCl under ice bath drops (127.5g, 1 . 258 muM, 0 . 5eq.) dropping process temperature can be raised to reflux, then completing, reflux 6h. LC - Ms detection reaction is complete; reducing pressure and solvent, a brown yellow liquid 491.56g, yield (theoretical): 100%. The crude product directly into the next step.
  • 3
  • [ 18718-79-1 ]
  • [ 65275-12-9 ]
  • [ 1254781-36-6 ]
YieldReaction ConditionsOperation in experiment
43% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; for 20h;Inert atmosphere;Product distribution / selectivity; To a stirred solution of <strong>[18718-79-1](5-methyl-3-phenyl-4-isoxazolyl)methanol</strong> (570 mg, 3.01 mmol) and 5- hydroxy-pyridine-2-carboxylic acid ethyl ester (655 mg, 3.92 mmol) in THF (15 mL) under argon was added triphenylphosphine (1.03 g, 3.93 mmol). Diethyl azodicarboxylate (1.71 mL of a 40% solution in toluene, 682 mg, 3.92 mmol) was added dropwise. After 20 h the reaction mixture was concentrated in vacuo, water was added, and the reaction mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 10 to 60% ethyl actetate in heptane) afforded the title compound (440 mg, 43%) as a pink oil. MS: m/e = 339.3 [M+H]+.; To a solution of <strong>[18718-79-1](5-methyl-3-phenyl-isoxazol-4-yl)-methanol</strong> (870 mg, 4.6 mmol) in THF (30 mL) was added 5-hydroxy-pyridine-2-carboxylic acid ethyl ester (999 mg, 6.0 mmol) and triphenylphosphine (1.57 g, 6.0 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (2.74 mL, 40% solution in toluene, 6.0 mmol) was added and the reaction mixture was stirred for 24 h at room temperature. The reaction mixture was evaporated and then diluted with water (40 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried, filtered and concentrated in vacuo. Purification by chromatography (silica, heptane:ethyl acetate = 100:0 to 2:3) afforded the title compound (481 mg, 31%) as a light yellow solid after trituration with dichloromethane. MS: m/e = 339.3 [M+H]+.
  • 4
  • [ 65275-12-9 ]
  • [ 1416134-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: rhodium contaminated with carbon; hydrogen / ethanol / 12 h / 20 °C / 10343.2 Torr 2.1: Lipozyme CALB / aq. phosphate buffer / 12 h / 20 °C / pH 7.5 / Enzymatic reaction 3.1: triethylamine / water; tetrahydrofuran / 18 h / 0 - 20 °C 4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / acetonitrile / -30 °C 4.2: 12.5 h / -30 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 15 h / 0 - 20 °C 6.1: ammonia; methanol / 8 h / 20 °C
Multi-step reaction with 6 steps 1.1: hydrogen; 10% rhodium on carbon / ethanol / 12 h / 10343.2 Torr 2.1: novozymes CALB / aq. phosphate buffer / 12 h / 20 °C / pH 7.5 / Enzymatic reaction 3.1: triethylamine / water; tetrahydrofuran / 18 h / 20 °C 4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / acetonitrile / 0.25 h / -30 °C 4.2: 12.5 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 15 h / 0 - 20 °C 6.1: ammonia / methanol; toluene / 0 - 20 °C / Saturated gas
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