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[ CAS No. 1827-27-6 ] {[proInfo.proName]}

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Chemical Structure| 1827-27-6
Chemical Structure| 1827-27-6
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Product Details of [ 1827-27-6 ]

CAS No. :1827-27-6 MDL No. :MFCD01632180
Formula : C5H5FN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :YTHMOBMZVVFNBE-UHFFFAOYSA-N
M.W : 112.11 Pubchem ID :819440
Synonyms :

Safety of [ 1827-27-6 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338-P310 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1827-27-6 ]

* 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 [ 1827-27-6 ]

[ 1827-27-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 456-24-6 ]
  • [ 1827-27-6 ]
YieldReaction ConditionsOperation in experiment
75% With 5%-palladium/activated carbon; hydrogen; sodium sulfate; In toluene; for 15h; 0.282 g of 5% Pd / C and lOmmol of anhydrous sodium sulfate were added to a 100 mL round bottom flask containing 50 mmol of <strong>[456-24-6]5-nitro-2-fluoropyridine</strong> in 50 ml of toluene, then hydrogen gas was added and heated and stirred for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, suction filtered, spin-evaporated, recrystallized and dried in vacuo to give 1.6806 g of 5-amino-2-fluoropyridine as a solid product in 75% yield.
70% With hydrogen;nickel; In ethyl acetate; for 18h; To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70 C. for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30% ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84%) of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> as an oil, which was used in the following procedure. To 76 g of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70%) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91 C.; mass spectrum (m/e): M+H 112.7.
70% To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70C for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30% ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84%) of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> as an oil, which was used in the following procedure. To 76 g of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70%) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91C; mass spectrum (m/e): M+H 112.7.
palladium on charcoal; In toluene; Method A Preparation of 5-Amino-2-fluoropyridine A solution of 5 g (35 mmol) <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 100 mL of toluene was hydrogenated over a mixture of 5% palladium on charcoal and anhydrous sodium sulfate until the uptake of hydrogen ceased. The solids were filtered off, the residue was washed with ethyl acetate, and the combined organic solutions were evaporated to give 3.7 (94%) of 5-amino-2-fluoropyridine as a white solid. Recrystallization from dichloromethane-hexanes gave the product mp 89-90 C. (literature mp 87-87.5 C.; Finger G. C., Starr L. D., Roe A., and Link W. J., J. Org. Chem., 27:3965-3968 (1967)). 1H NMR (CDCl3): delta7.62 (t, J=2.3 Hz, 1H), 7.11 (td, J=7.7, 3.0 Hz, 1H), 6.72 (dd, J=8.7, 3.3 Hz, 1H), and 3.74 (br s, 2H).
30.9 g (75%) palladium-carbon; In ethanol; 12b. 5-Amino-2-fluoropyridine <strong>[456-24-6]<strong>[456-24-6]2-Fluoro-5-nitropyridin</strong>e</strong> (52.35 g, 368 mmol, from step 12a) was combined with 5% Pd/C (100 mg) in EtOH (100 mL), and the mixture was stirred under a H2 atmosphere for 4 days. The mixture was filtered and concentrated, and the residue was chromatographed (silica gel;/EtOAc/hexane, 1:9 to 1:1) to afford 30.9 g (75%)of the title compound: 1 H NMR (DMSOd-6 300 MHz) delta6.74 (dd, J=3, 6 Hz, 1H), 7.11 (m, 1H), 7.26 (t, J=1 Hz, 1H); MS (CI/NH3) m/z: 113 (M+H)+, 130 (M+NH4)+.
30.9 g (75%) palladium-carbon; In ethanol; 8c. 3-Amino-6-fluoropyridine <strong>[456-24-6]<strong>[456-24-6]2-Fluoro-5-nitropyridin</strong>e</strong> (52.4 g, 368 mmol, from Step 8b above) was combined with 5% Pd/C (100 mg, Aldrich) in EtOH (100 mL) and the mixture was stirred under a H2 atmosphere for 4 days. The mixture was filtered and concentrated. The crude product was chromatographed (silica gel; hexane/EtOAc, 9:1 to 1:1) to give 30.9 g (75%) of the title compound: 1 H NMR (DMSO-d6, 300 MHz) delta 6.74 (dd, J=3, 6 HzH, 1 H), 7.11 (m, 1 H), 7.26 (t, J=1 Hz, 1 H), MS (CI/NH3) m/z 113 (M+H)+, 130 (M+NH4)+.

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