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CAS No. : | 55304-73-9 | MDL No. : | MFCD07369746 |
Formula : | C6H3Cl2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HWTMRGXKSANEDO-UHFFFAOYSA-N |
M.W : | 176.00 | Pubchem ID : | 12259383 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
80% | With Dess-Martin periodane; In dichloromethane; at 20 - 26℃; for 2.0h; | To a solution of <strong>[55304-90-0](2,6-dichloropyridin-3-yl)methanol</strong> (1.0 g, 5.62 mmol) in CH2C12 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5% aqueous Na2S203 and stirred for 30 min. The resulting mixture was extracted with CH2C12 (2x30 ml). The combined organic layers were washed with saturated Na2S203 solution (50 ml), brine (30 ml), dried over Na2S04 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80%). 1H NMR (400MHz, CDC13): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H). |
66% | With pyridinium chlorochromate; In dichloromethane; for 2.0h; | Dissolve <strong>[55304-90-0](2,6-dichloropyridin-3-yl)-methanol</strong> (876 mg, 4.92 mmol) in dichloromethane (20.mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite and silica gel and concentrate to give 2,6-dichloropyridine-3-carbaldehyde (575 mg, 66%): 1H NMR (400 MHz5 CDCl3) delta 10.39 (s, IH)5 8.18 (d, IH, J = 8.0 Hz)5 7.43 (d, IH, J = 8.0 Hz). |
With manganese dioxide; In benzene; | 180 g (1.01 mols) of <strong>[55304-90-0]2,6-dichloro-3-hydroxymethylpyridine</strong> are then heated under reflux for 2 hours with 600 g (6.9 mols) of manganese dioxide in 4 l of benzene. The reaction mixture is filtered while still hot and the benzene is evaporated. After drying the residue in a vacuum drying cabinet, 2,6-dichloropyridine-3-aldehyde is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2 - Synthesis of Phantasmidine (Figure 2) 2,6-Dichloropyridine-3-pyridinemethanol (9a). A solution of 2,6- dichloropyridine-3-carboxaldehyde (8a) (950 mg, 5.40 mmol) in MeOH (10 mL) was treated with NaBH4 (205 mg, 5.40 mmol) in one portion at 0 C. The reaction was stirred at 0 C for 30 min. 10% aqueous hydrochloric acid was added dropwise to the reaction until pH 1 was reached and MeOH was removed under vacuum. The residue was extracted with CH2CI2 (50 mL x 3). The combined CH2CI2 layers were washed with H20 (50 mL) and brine (50 mL), dried (Na2S04), and concentrated to give 952 mg (99%) of 9a as a white solid, which was used directly without further purification. A small portion of crude 9a was recrystallized to give an analytical sample: mp 73-74 C (lit. 62-64 C); 1H NMR 7.88 (d, 1, J = 8.0), 7.33 (d, 1, J = 8.0), 4.78 (br s, 2), 2.21 (br s, 1, wm = 16, OH); 13C NMR 148.8, 147.8, 139.1, 133.8, 123.2, 60.9; IR 3369. The data are identical to those previously reported. | ||
3.01 g | With methanol; sodium tetrahydroborate; at 20℃; for 0.5h; | [1037] NaBH4 (808 mg, 21.3 mmol) was added to a solution of 514-1 (3.10 g, 17.7 mmol) in MeOH (22 niL), which had been pre-cooled to 0 C. The mixture was allowed to reach r.t. and stirring was prolonged for 30 mins. 1 M aq. HC1 solution was added, and the organic solvent was removed under reduced pressure. The aqueous phase was extracted with DCM (3x). The combined organic portions were dried with and filtered. The volatiles were removed under reduced pressure to afford 514-2 (3.01 g). UPLC/MS(ES+): m/z 178.00 [M+H]+. |
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