Structure of 194151-96-7
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CAS No. : | 194151-96-7 |
Formula : | C8H11NO |
M.W : | 137.18 |
SMILES Code : | OCC=1C(=NC=CC1C)C |
MDL No. : | MFCD16988725 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
100% | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (2 g, 11.2 mmol) in anhydrous THF (10 mL), previously cooled to -10C, was added 2.4M lithium aluminium hydride (9.3 mL, 22.4 mmol) portionwise. Stirring was continued for 16 h. Water (0.8 mL) was added dropwise, followed by 15% aqueous sodium hydroxide solution (0.8 mL), then more water (2.4 mL). The reaction mixture was stirred at r.t. for 1 h, then extracted with DCM (2 x 100 mL). The organic phases were combined, dried over Na2S04 and filtered. The solvent was removed in vacuo to give the title compound (1.53 g, 100%) as a white solid. Method B HPLC-MS: MH+ mlz 138, RT 0.26 minutes | |
87.53% | With lithium aluminium tetrahydride; In tetrahydrofuran; at -30 - -10℃; for 3h;Inert atmosphere; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (1 g, 5.58 mmol, 1 equiv.) in THF (40 mL) was batch added LiAlH4(317.7 mg, 8.37 mmol, 1.50 equiv.) at -30 degrees Celsius under nitrogen atmosphere. The resulting mixture was stirred for 3h at -30 degrees Celsius~ -10 degrees Celsius. The desired product could be detected by LCMS and TLC. The reaction mixture was quenched with water(0.5mL) at -30 degrees Celsius and quenched with 15% NaOH(aq). The mixture was filtrated, the filtrate was concentrated under reduced pressure to crude product. The crude product was purified by Prep-TLC (PE / EA 1:1) to afford (2,4-dimethylpyridin-3- yl)methanol (670 mg, 87.53%) as a white solid. |
84.9% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (1.0 g, 5.57 mmol) in dry tetrahydrofuran (10 mL), lithium alu minum hydride (1.0 M solution in THF, 8.36 mL, 8.36 mmol) was added at 0C during 30 minutes and stirred at rt for 1.5h. After 1.5 h, excess of LiA1H4 was decomposed with crushed ice and the residue was extracted with ethyl acetate (300 mL). The combined organic layers were dried over Na2SO4 and concentrated and the product was purified by silica gel column chromatography (2.5% MeOH: dichloromethane) to provide the title compound (0.650 g, 84.9%), 1H (400 MHz, DMSO-d6) delta ppm 8.16-8.18 (d, 1H), 7.01-7.02 (d, 1H), 4.89-4.92, (t, 1H), 4.50-4.51 (d, 2H), 2.50 (s, 3H), 2.34 (s, 3H). |
67% | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (5.35 g, 30 mmol) in DCM (150 mL) under argon at -78 0C was added diisobutylaluminium hydride (IM in hexane, 100 mL, 100 mmol). The reaction mixture was stirred for 24 hours and then added to a saturated aqueous solution of Rochelle salt (200 mL) at 0 0C. The mixture was stirred until two layers had formed. The phases were separated and the aqueous phase was extracted with DCM (2 x 150 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from EtOAc to give (2,4-dimethyl- pyridin-3-yl)-methanol (2.76 g, 67%) as a pale yellow solid. Analytical LCMS: (System A, Rtau = 0.46 min), ES+: 138.0 [MH]+. | |
54.8% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; | To a stirred solution of2,4-Dimethyl-nicotinic acid ethyl ester (6) (500 mg, 2.79 mmol) in THF (10 mL) was cooled to 0C and LiAlH4 (424 mg, 11.159 mmol) was added and the resultant reaction was stirred at Rt for 2 hour. The reaction was quenched with 2N NaOH solution and stirred for 10 min. The reaction mixture was then filtered off and washed with ethyl acetate. The filtrate was then further washed with brine, dried over sodlium sulfate and concentrated to afford Intermediate 7 (210 mg, 54.8%) as yellow gum. |
Example 31 : 4-Chloro-N-[5-chloro-2-(2,4-dimethyl-pyridine-3-carbonyl)-Pyridin-3- yl]-3-trifluoromethyl-benzenesulfonamide; [00416] Step 1 : A solution of lithium aluminum hydride in THF (1.0 M, 40 mL, 40 mmol) placed in a 100-mL round bottom flask equipped with a magnetic stirring bar was cooled in an ice bath and cautiously treated with a solution of <strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (5.4 g, 30 mmol) in anhydrous THF (10 mL) over 5 min period. After the addition was complete the cold bath was removed and the mixture was allowed to stir at room temperature for 2 h. The reaction mixture was then cooled in an ice bath and the excess LAH was quenched by drop wise addition of water until gas evolution stopped. The reaction mixture was then basified with 2M NaOH to pH 9-10. Ether (100 mL) was added the mixture was washed with 1 M NaOH, water and brine. The organic layer was EPO <DP n="112"/>dried over MgSO4 and the solvent was evaporated to yield (2,4-dimethyl-pyridin- 3-yl)-methanol as a white solid. MS: (M+H) /z = 138. | ||
With sodium hydroxide; In tetrahydrofuran; water; | Step 1: Preparation of 3-hydroxymethyl-2,4-dimethylpyridine To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (3.00 g) in tetrahydrofuran (30 mL), lithium aluminum hydride (1.21 g) was added portionwise with ice-bath cooling. After stirring for 2 hours, water (1.2 mL), 15% aqueous sodium hydroxide (1.2 mL) and water (3.6 mL) were successively added to the resulting reaction mixture and the mixture was stirred at room temperature. The organic layer was obtained, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (2.26 g) as white crystals. | |
With diisobutylaluminium hydride; In dichloromethane; at -70℃; for 2h; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (538 mg, 3 mmol) in DCM (5 ml) was added dropwise, at -70C, DIBAL-H 1 M in DCM (8 ml, 8 mmol). The reaction mixture was stirred at this temperature during 2 h. The reaction mixture was quenched by a slow addition of EtOAc (1 ml) and H20 (1 ml), then concentrated. The crude residue was purified by flash chromatography on silica gel (gradient EtOAc then DCM/MeOH 95/5 to 9/1 ). TLC, Rf (DCM/MeOH 9/1 ) = 0.22; [M+H]+ = 138.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Step 2. The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0 C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0 C. and quenched with EtOAc (2.5 mL), then H2 O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2 O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine. |
Tags: 194151-96-7 synthesis path| 194151-96-7 SDS| 194151-96-7 COA| 194151-96-7 purity| 194151-96-7 application| 194151-96-7 NMR| 194151-96-7 COA| 194151-96-7 structure
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