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CAS No. : | 491-34-9 | MDL No. : | MFCD00130001 |
Formula : | C10H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YVBSECQAHGIWNF-UHFFFAOYSA-N |
M.W : | 147.22 | Pubchem ID : | 68109 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.24 |
TPSA : | 3.24 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.47 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 2.44 |
Log Po/w (WLOGP) : | 1.69 |
Log Po/w (MLOGP) : | 2.37 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 2.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.69 |
Solubility : | 0.298 mg/ml ; 0.00202 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.15 |
Solubility : | 1.04 mg/ml ; 0.00706 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.93 |
Solubility : | 0.173 mg/ml ; 0.00118 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
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: |
* 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 |
---|---|---|
12% | With IrCl3·3H3O; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,3,5-trimethyl-benzene at 165℃; for 18 h; | Eq. 2 : To a vial was added 8 (1.0 mmol, 151.3 mg), 3a (1.0 mmol, 107.3 mg), IrCl3·3H3O(5.0 molpercent, 17.6 mg), rac-BINAP (7.5 molpercent, 46.7 mg) under air. To the vial was addedmesitylene (1.0 mL) and stirred at 165 °C for 18 h. After the reaction, the resulting residue waspurified by flash column chromatography on SiO2 (tBuOMe:Hexane=1:15) to yield 5a and 3a asa mixture and 4a (19.7 mg) in 21percent yield. Then PTLC (Wako Silicagel 70 PF254 Plate-Wako,tBuOMe:Hexane=1:15) was used for purification to give 5a (20.3 mg) in 12percent yield (based onstarting material) and 3a (76.8 mg) in 52percent yield, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 2h; | Here, 13.99 g of 1,2,3,4-tetrahydroquinoline and 14.52 g of potassium carbonate were dissolved into 350 ml of methanol. The resultant solution was maintained at temperatures between 45C and 50C with constant mixing. To this solution, 25.54 g of dimethyl sulfate was added dropwise. Subsequently, the solution was stirred for 3 hours at temperatures between 45C and 50C. Thereafter, the solution was left overnight. For toluene extraction, 350 ml of toluene and 350 ml of water were added to this solution. The extracted toluene solution was dried using anhydrous sodium sulfate, followed by removal of toluene to obtain a brown solution. This solution was column-purified to obtain 12.9. g of a pale yellow solution represented by the following structural formula (e). [Show Image] Here, 12.9 g of the compound represented by the above structural formula (e) was added dropwise to 230 g of concentrated sulfuric acid which had been cooled to between 0C and 5C, while maintaining the temperature at 0C to 5C. Subsequently, a mixture of 36 g of concentrated sulfuric acid and 9.0 g of concentrated nitric acid was added dropwise to the resultant solution while maintaining the temperature at 0C to 5C. After the mixture solution was added, the solution was returned to room temperature, followed by stirring for 2 hours. The reacted solution was poured into 300 ml of ice water for cooling. Then, the solution was adjusted to pH 9 by the addition of 50% aqueous sodium hydroxide while cooling the solution. After stirring for 1 hour, the deposited crystal was separated by filtration and dried. Thus, 12.4 g of red crystal represented by the following structural formula (f) was obtained. [Show Image] Here, 31.4 g of iron powder was suspended in 183 ml of DMF-water (2: 1) solution, and the solution was heated to between 85C and 90C with constant mixing. To this solution, a mixture obtained by mixing 6.7 ml of hydrochloric acid with 91.5 ml of DMF-water (2:1) solution was added dropwise. Subsequently, while maintaining the temperature at 85C to 95C, 183 ml of DMF solution containing 12.0 g of the compound represented by the above structural formula (f) was added dropwise to this solution by taking 15 minutes. The resultant solution was stirred for 20 minutes at the temperature between 80C to 90C. Thereafter, while the solution was left for cooling, 6.39 g of sodium hydrogencarbonate was added thereto, followed by stirring for 10 minutes. The solution was then filtrated to remove iron powder, and the filtrate was poured into 500 ml of ice water for toluene extraction. After the resultant solution was dried using anhydrous sodium sulfate, toluene was removed to obtain 5.47 g of a brown liquid represented by the following structural formula (g). [Show Image] Under nitrogen flow, 9.31 g of trifluoromethanesulfonic anhydride was stirred, and was maintained a temperature of 20C or below. Here, 40 ml of toluene solution containing 5.47 g of the compound represented by the above structural formula (g) was added dropwise. The resultant solution was subsequently stirred for 4 hours at the temperature between 10C and 15C. Thereafter, the solution was left overnight. To the reacted solution, 2 ml of water is added at the temperature between 10C to 25C and was stirred for 1 hour. Thereafter, the deposited solid substance was the separated by filtration. The substance thus harvested was then dissolved into ethyl acetate, and 150 ml of water was added thereto. Then, the resultant solution was extracted with ethyl acetate. After the resultant solution was dried using anhydrous sodium sulfate, ethyl acetate was removed to obtain 6.87 g of a dark brown liquid represented by the following structural formula (h). [Show Image] [Show Image] Here, 0.58 g of 2-amino-5-methyl-1,3,4-thiadiazole represented by the above-described structural formula (i) was dissolved into a mixture of 5ml of acetic and 3 ml of propionic acid. To this solution, 1 ml of sulfuric acid was added dropwise at the temperature between 0C and 5C. Then, 1.78 g of 43% nitrosylsulfuric acid was added dropwise to the resultant solution at the temperature between 0C and 5C. In this way, diazotization was performed. Then, 1.77 g of the compound represented by the structural formula (h), 0.2 g of urea and 2.0 g of sodium acetate were dissolved into 20 ml of methanol. To this solution, the resultant diazo solution was added dropwise at the temperature between 0C and 5C and was stirred for 3 hours. Thereafter, the resultant solution was left overnight. The deposited crystal was separated by filtration and then dried. Thus, 1.44 g of red crystal was obtained which is represented by the following structural formula (j). [Show Image] Here, 1.30 g of an azo-compound represented by the structural formula (j), which was obtained as described above, was dissolved into 50 ml of THF. At room temperature, 6 ml of methanol solution containing 0.46 g of nickel acetate tetrahydrate was then added to the resultant... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium cyanoborohydride; acetic acid; In ethanol; for 18h; | 1,2,3,4-tetrahydroquinoline (10 g, 75.2 mmol)) was dissolved in ethanol (100 mL). 20 mL of 37% formaldehyde was added, followed by addition of NaCNBH3 (9.4 g) and 1 mL of AcOH. The reaction was stirred for 18 hours. The reaction mixture was treated with 100 mL of saturated ammonium chloride and stirred for 1 hour. After removal of ethanol in vacuo, the remaining solution was extracted with 200 mL of dichloromethane twice. The combined organic layer was washed with saturated NaCl, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatograph with hexane -ethyl acetate to afford 1 -methyl - 1,2,3,4-tetrahydroquinoline as a clear oil (yield: 90%). H NMR (CDC13): delta 7.13 (t, 1H), 7.0 (t, 1H), 6.63(m, 2H), 3.26 (t, 2H), 2.90 (s, 3H), 2.80 (m, 2H), 2.01 (t, 2H). |
52.9% | Step A: AcOH (210 mg, 3.5 mmol) was added to a mixture of 1,2,3,4-tetrahydroquinoline (2.0 g, 15.0 mmol) andparaformaldehyde (6.77 g, 75.1 mmol) dissolved in MeOH (20 mL) in one portion at 25C. The mixture was stirredat 25C for 1 hour, followed by the addition of NaBH3CN (1.89 g, 30.0 mmol) and continuous stirring for 16 hours.The mixture was concentrated under reduced pressure. The residue was poured into water (15 mL) and stirred for10 min. The aqueous phase was extracted with ethyl acetate (10 mL 3 3). The combined organic phase was washedwith saturated brine (10 mL 3 3), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum, to give1-methyl-1, 2,3,4-tetrahydroquinoline (1.17 g, 52.9 %) as a yellow oil. MS (ESI) M/Z: 148 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4- tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C and the resulting suspension was maintained at 0-5 C for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford l-methyl-1,2,3,4- tetrahydroquinoline in 61% yield as a yellow liquid. | |
61% | Intermediate 11: Synthesis of 1-methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride; 1. Synthesis of 1-methyl-1,2,3,4-tetrahydroquinoline; Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C. and the resulting suspension was maintained at 0-5 C. for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford 1-methyl-1,2,3,4-tetrahydroquinoline in 61% yield as a yellow liquid. | |
61% | Intermediate 17: Synthesis of l-methyl-l,2,3,4-tetrahydroquinoline-7-sulfonyl chloride.1. Synthesis of 1 -methyl- 1 ,2,3,4-tetrahydroquinoline.Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4- tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C and the resulting suspension was maintained at 0-5 0C for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford 1 -methyl- 1, 2,3, 4-tetrahydroquinoline in 61% yield as a yellow liquid. |
61% | With sodium hydride; In tetrahydrofuran; at 0 - 20℃; | Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C. and the resulting suspension was maintained at 0-5 C. for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford 1-methyl-1,2,3,4-tetrahydroquinoline in 61% yield as a yellow liquid. |
61% | Intermediate 17: Synthesis of l-methyl-l,2,3,4-tetrahydroquinoline-7-sulfonyl chloride. 1. Synthesis of 1 -methyl- 1 ,2,3,4-tetrahydroquinoline.Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4- tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C and the resulting suspension was maintained at 0-5 0C for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford 1 -methyl- 1, 2,3 ,4-tetrahydroquinoline in 61% yield as a yellow liquid. | |
61% | Sodium hydride (300 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (200 mmol) in tetrahydrofuran (150 mL) at 0-5 C. and the resulting suspension was maintained at 0-5 C. for 30 min. Iodomethane (352 mmol) was added dropwise and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The mixture was filtered and the filtrate was purified by Flash chromatography (1/100 ethyl acetate/petroleum ether) to afford 1-methyl-1,2,3,4-tetrahydroquinoline in 61% yield as a yellow liquid. | |
61% | NaH (12 g, 60%, 300.00 mmol) was added in several batches, to a solution of 1,2,3,4- tetrahydroquinoline (26.6 g, 199.70 mmol) in tetrahydrofuran (150 mL) at 0-5 0C. The resulting solution was maintained at 0-5 0C for 30 minutes, then iodomethane (50 g, 352.11 mmol) was added dropwise (at 0-5 0C). The resulting solution was then stirred at room temperature overnight. The mixture was filtered, and the filtrate was purified by column chromatography using a 1:100 ethyl <n="127"/>acetate/petroleum ether solvent system to afford 19 g (61%) of l-methyl-l,2,3,4-tetrahydroquinoline as a yellow liquid. | |
56% | With sodium hydride; In tetrahydrofuran;Inert atmosphere; Cooling with ice; | Under argon atmosphere, NaH (2.4 g, 99 mmol) was added to anhydrous THF, 1,2,3,4-tetrahydroquinoline (8.8 g, 66 l mmol) was added under ice-cooling, Mel (16.9 g, 66 l mmol) and reacted in an ice bath overnight to room temperature. After the reaction was stopped, the mixture was diluted with water, extracted with DCM, dried, and the column was separated to give a pale brown oil (5.5 g, 56%) |
Reference Example 96 Under an argon atmosphere, to a suspension of sodium hydride (1.44 g) in DMF (150 ml) was added dropwise a solution of 1,2,3,4-tetrahydroquinoline (4.0 g) in DMF (20 ml) at 0C. After stirring for 1 hour at 0C, iodomethane (2.06 ml) was added to the reaction system at 0C, and the mixture was stirred for 12 hours at room temperature. To the reaction system was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by column chromatography (ethyl acetate: hexane 1: 19) to give 1-methyl-1,2,3,4-tetrahydroquinoline (3.64 g) as a colorless oily material. 1H-NMR (300 MHz, CDCl3) delta 1.94-2.02 (2H, m), 2.76 (2H, t, J=6.6 Hz), 2.88 (3H, s), 3.21 (2H, t, J=5.7 Hz), 6.57-6.62 (2H, m), 6.93-6.96 (1H, m), 7.04-7.25 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-Bromosuccinimide; In tetrahydrofuran; at -78 - 20℃; for 19h;Inert atmosphere; | Synthesis of 332 To a tetrahydrofuran (70 ml) solution of 331 (5.25 g, 35.66 mmol), N-bromosuccinimide (6.35 g, 35.66 mmol) was added at -78C under an argon atmosphere, and the mixture was stirred at the same temperature for 3 hours, followed by stirring at room temperature for 16 hours. To the reaction solution, water and ethyl acetate were added, and the solution was extracted with ethyl acetate after adjusting the pH to 9 using an aqueous potassium carbonate solution. The extraction liquid was dried and the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane = 1/50) to obtain 332 (7.38 g, 91%) as a colorless oily substance. APCI-MS m/z 226/228[M+H]+ |
With tetrabuthylammonium tribromide; In dichloromethane; at 0 - 20℃; for 18.5h; | Reference Example 97 To a solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (3.64 g) in dichloromethane (50 ml) was added tetrabutylammonium tribromide (11.92 g) at 0C. The mixture was stirred for 30 minutes at 0C and for 18 hours at room temperature. Water was added to the reaction system, and the mixture was extracted with dichloromethane. The organic layer was washed with an aqueous sodium thiosulfate solution and saturated brine, and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by column chromatography (ethyl acetate: hexane 1: 19) to give 6-bromo-<strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (4.65 g) as a pale yellow oily material. 1H-NMR (200 MHz, CDCl3) delta 1.89-2.01 (2H, m), 2.73 (2H, t, J=6.4 Hz), 2.85 (3H, s), 3.20 (2H, t, J=5.7 Hz), 6.43 (1H, d, J=8.6 Hz), 7.02-7.05 (1H, m), 7.10-7.16 (1H, m). IR (neat) 1501, 1323, 1208, 912, 740 cm-1 | |
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 25℃; for 18h; | Step B: A solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (300 mg, 2.04 mmol) in DMF (5 mL) was cooled down to0C and then added with NBS (363.1 mg, 2.0 mmol). The reaction solution was stirred at 0C for 2 hours and thenwarmed up to 25C with stirring for 16 hours. The reaction substances were then poured into 5 mL of water and thesuspension was extracted with ethyl acetate (5 mL 3 3). The combined organic phase was washed with saturatedbrine (5 mL 3 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum, to give the crudeproduct 6-bromo-<strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (485 mg) as a brown solid, which was used in the next stepwithout further purification. MS (ESI) M/Z: 226 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; In sodium hydroxide; acetic acid; acetonitrile; | PREPARATION H 1-Methyl-1,2,3,4-tetrahydroquinoline 1,2,3,4-tetrahydroquinoline (2.0 g, 0.0015 mol) and formaldehyde (12 ml of 38% aqueous, 0.015 mol) were combined in 60 ml CH3 CN. NaBH3 CN (2.85 g) and then, over a 10 minute period, glacial acetic acid (1.50 ml) were added and the mixture stirred 2 hours, at which time additional acetic acid (0.5 ml) was added. After stirring an additional 30 minutes, the reaction mixture was poured into 200 ml ether, washed 3*30 ml IN NaOH, dried (K2 CO3) and stripped in vacuo to yield title product, 2.27 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 21 1-Methyl-1,2,3,4-tetrahydro-6-quinoline carbaldehyde By the method of Example 5, <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (2.27 g, 0.015 mol) was converted to present title product as an oil, purified by flash chromatography on 4 cm*40 mm of silica gel with CH2 Cl2 as eluant, 1.84 g. | ||
With trichlorophosphate; In N-methyl-acetamide; | b. 6-formyl-<strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>. 31 ml of phosphorus oxychloride is added dropwise while stirring and cooling in ice into 100 ml of dimethylformamide. To the stirred and cooled solution is added by portions 50.0 g of <strong>[491-34-9]N-methyl-1,2,3,4-tetrahydroquinoline</strong>. After the addition the mixture is heated on a steam bath for 1 hour. The liquid is cooled and poured into 1 l of crushed ice. The solution is alkalized with sodium hydroxide and extracted with ether. The extract is dried over anhydrous sodium sulphate and the solvent evaporated. The residual oil is distilled. Yield: 47.4 g, b.p. 175-178 /6 mm. Equiv. weight 178 (calc. 175.23). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; | EXAMPLE 2 Preparation of 1-methyl-1,2,3,4-tetrahydroquinoline (kairoline M)(IA,R=methyl) N-Methylquinolinium methosulfate 450 g. and platinum oxide 5.0 g. in methanol 1.2 l. were agitated and warmed to 45 in a Parr 2 l. hydrogenator. Hydrogen uptake was theoretical and complete in two and a half hours. The solution was filtered and evaporated to dryness, and the catalyst reused. The amber gum was dissolved in dichloromethane 800 ml., which was washed with 10% aqueous sodium hydroxide 800 ml., water 800 ml., and was dried over sodium sulfate. Evaporation of the solvent left a light brown mobile oil 260 g. Several hydrogenation fractions were combined 830 g. and distilled, and the fraction boiling between 75 and 79 at 1 mm. collected as kairoline 762 g. (92%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydroxide; In water; | EXAMPLE 5 Synthesis of 2,2-bis(<strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-yl)propionic acid Into 6.0 ml of 6N--HCl solution was dissolved 4.2 g of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>. To the solution was added 3 g of pyruvic acid and the mixture was heated with reflux for 20 hours. The reaction mixture was, after cooled, diluted with 100 ml of water and adjusted to pH 6 with addition of 20% aqueous solution of sodium hydroxide. The precipitated crystal was collected by filtration which was 4.0 g (yield 77%) of 2,2-bis(<strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-yl)propionic acid as light brown crystal, having a melting point of 155~157 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; for 16h; | A solution of 1 -methyl- 1, 2,3, 4-tetrahydroquinoline (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 C and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford 1-methyl- 1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride in 8% yield as a yellow liquid. 1H NMR (CDCl3) delta 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | 2. Synthesis of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-7-sulfonyl chloride; A solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 C. and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3×150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-7-sulfonyl chloride in 8% yield as a yellow liquid. Data: 1H NMR (CDCl3) delta 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | 2. Synthesis of 1 -methyl- 1, 2,3, 4-tetrahydroquinoline-7-sulfonyl chloride.A solution of 1 -methyl- 1,2,3, 4-tetrahydroquinoline (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 0C and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford 1 -methyl- 1, 2,3, 4-tetrahydroquinoline-7-sulfonyl chloride in 8% yield as a yellow liquid. 1H NMR (CDCl3) delta 7.19 (d, IH), 7.10 (d, IH), 7.06 (s, IH), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | A solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 C. and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3×150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-7-sulfonyl chloride in 8% yield as a yellow liquid. 1H NMR (CDCl3) delta 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | 2. Synthesis of 1 -methyl- 1,2,3, 4-tetrahydroquinoline-7-sulfonyl chloride.A solution of 1 -methyl- 1, 2,3, 4-tetrahydroquinoline (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 0C and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford l-methyl-l,2,3,4-tetrahydroquinoline-7-sulfonyl chloride in 8% yield as a yellow liquid. 1H NMR (CDCl3) delta 7.19 (d, IH), 7.10 (d, IH), 7.06 (s, IH), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | A solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (68.0 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 0-5 C. and the reaction mixture was allowed to warm to rt and was maintained for 16 h. The reaction mixture was diluted with iced water (300 mL) and was extracted with ethyl acetate (3*150 mL). The organic layers were combined, concentrated, and the residue was purified by Flash chromatography (1/20 ethyl acetate/petroleum ether) to afford <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-7-sulfonyl chloride in 8% yield as a yellow liquid. Data: 1H NMR (CDCl3) delta 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
8% | With chlorosulfonic acid; In dichloromethane; at 0 - 20℃; | A solution of l-methyl-l,2,3,4-tetrahydroquinoline (10 g, 68.03 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 0-5 0C, and the resulting solution was maintained at room temperature overnight. The reaction mixture was then quenched by adding300 mL of iced water. The resulting solution was extracted using ethyl acetate (3 x 150 mL). The organic layers were combined, concentrated, and the residue was purified by column chromatography using a 1:20 ethyl acetate/petroleum ether solvent system to afford 1-methyl-l, 2,3,4- tetrahydroquinoline-7-sulfonyl chloride as a yellow liquid in 8% yield. 1H NMR (CDCl3) delta 7.19 (d,IH), 7.10 (d, IH), 7.06 (s, IH), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H). |
With chlorosulfonic acid; In dichloromethane; for 20h;Inert atmosphere; Cooling with ice; | Under the protection of the Ar, cryohydrate under bath, 1 - methyl tetrahydroquinoline (6.5 g, 44.2 mmol) dissolved in anhydrous DCM, adding chlorosulfonic acid (30 ml), stirring reaction 20 h, stop in the system after the reaction slowly adding ice water, DCM extraction, the organic phase is dried, directly in the next step reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With sulfuric acid; In diethyl ether; for 5.5h;Inert atmosphere; Cooling with ice; | Ice bath conditions, <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (2.94 g, 20 mmol) Soluble in anhydrous ether, Sulfuric acid (2.35 g, 24 mmol) in ether was slowly added, After stirring, the ether was removed, Temperature response 5.5h. Stop the reaction after adding methanol dilute Release, near-white solid precipitation, filtration, EA / PE recrystallization, A white solid product (1.62 g, 36%) was obtained, Vacuum drying and argon protection for the next step |
34% | With sulfuric acid; In diethyl ether; at 5 - 170℃; for 3h; | A solution of sulfuric acid (60.0 mmol) in ether (40 mL) was added dropwise to a solution of 1- methyl- 1,2,3, 4-tetrahydroquinoline (61.1 mmol) in diethylether (10 mL) at 5 C. The diethylether was decanted and the resulting solution was maintained for 3 h at 170 C. The reaction mixture was concentrated and the residue was diluted with methanol (100 mL). The precipitated solids were isolated by filtration and dried to provide l-methyl-1,2,3,4-tetrahydroquinoline-6-sulfonic acid in 34% yield as a white solid. |
34% | With sulfuric acid; In diethyl ether; at 5 - 170℃; | Intermediate 12: Synthesis of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-sulfonyl chloride; 1. Synthesis of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-sulfonic acid; A solution of sulfuric acid (60.0 mmol) in ether (40 mL) was added dropwise to a solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (61.1 mmol) in diethylether (10 mL) at 5 C. The diethylether was decanted and the resulting solution was maintained for 3 h at 170 C. The reaction mixture was concentrated and the residue was diluted with methanol (100 mL). The precipitated solids were isolated by filtration and dried to provide <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-sulfonic acid in 34% yield as a white solid. |
34% | With sulfuric acid; In diethyl ether; at 5 - 170℃; | Intermediate 18: Synthesis of l-methyl-l,2,3,4-tetrahydroquinoline-6-sulfonyl chloride.1. Synthesis of 1 -methyl- 1 ,2,3 ^-tetrahydroquinoline--sulfonic acid.A solution of sulfuric acid (60.0 mmol) in ether (40 mL) was added dropwise to a solution of 1 -methyl- 1, 2,3, 4-tetrahydroquinoline (61.1 mmol) in diethyl ether (10 mL) at 5 C. The diethyl ether was decanted and the resulting solution was maintained for 3 h at 170 0C. The reaction mixture was concentrated and the residue was diluted with methanol (100 mL). The precipitated solids were isolated by filtration and dried to provide l-methyl-1,2,3,4- tetrahydroquinoline-6-sulfonic acid in 34% yield as a white solid. |
34% | With sulfuric acid; In diethyl ether; at 5 - 170℃; | A solution of sulfuric acid (60.0 mmol) in ether (40 mL) was added dropwise to a solution of <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong> (61.1 nm-ol) in diethylether (10 mL) at 5 C. The diethylether was decanted and the resulting solution was maintained for 3 h at 170 C. The reaction mixture was concentrated and the residue was diluted with methanol (100 mL). The precipitated solids were isolated by filtration and dried to provide <strong>[491-34-9]1-methyl-1,2,3,4-tetrahydroquinoline</strong>-6-sulfonic acid in 34% yield as a white solid. |
34% | With sulfuric acid; In diethyl ether; at 5 - 170℃; for 3.5h; | solution of H2SO4 (6 g, 60.00 mmol) in ether (40 mL) was added dropwise to a solution of l-methyl-l,2,3,4-tetrahydroquinoline (9 g, 61.14 mmol) in diethylether (10 mL) at 5 0C. The resulting solution was maintained at room temperature for 30 minutes, then under vacuum, with stirring, for an additional 3 hours at 170 0C. The resulting mixture was washed with methanol (1 x 100 mL) and filtered to afford 5 g (34%) of l-methyl-l,2,3,4-tetrahydroquinoline -6-sulfonic acid as a white solid. |
Tags: 491-34-9 synthesis path| 491-34-9 SDS| 491-34-9 COA| 491-34-9 purity| 491-34-9 application| 491-34-9 NMR| 491-34-9 COA| 491-34-9 structure
[ 1049677-37-3 ]
1-Propyl-1,2,3,4-tetrahydroquinolin-7-amine
Similarity: 0.98
[ 90874-58-1 ]
7-Methyl-1,2,3,4-tetrahydroquinoline hydrochloride
Similarity: 0.90
[ 52601-70-4 ]
8-Methyl-1,2,3,4-tetrahydroquinoline
Similarity: 0.88
[ 20668-20-6 ]
3-Methyl-1,2,3,4-tetrahydroquinoline
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