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CAS No. : | 23687-26-5 | MDL No. : | MFCD04114862 |
Formula : | C9H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NGFCTYXFMDWFRQ-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 588991 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 hydrazine hydrate; at 80℃; under 4137.29 Torr; for 0.75h;Microwave irradiation; | A mixture of 1u (100 mg, 0.81 mmol), hydrazine hydrate (121.5mg, 2.43 mmol), and SS-Rh (370 mg, 2 molpercent Rh) were taken in an oven dried reaction tube equipped with screw cap. 0.5 ml of PEG-400 was added into the reaction mixture. The reaction was then irradiated in a microwave apparatus at 80°C , 80 W for 10 min with a pressure of 80 Psi. After cooling to ambient temperature in the microwave cavity the reaction mixture was extracted with ethyl acetate (3x2 ml) and water (1ml). The combined organic layer wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure and after purificationwith silica gel column chromatography (hexane: EtOAc= 90:10) 2u asyellowish liquid (63 mg, 80percent).1H and 13C NMR spectra hasbeen compared with our previously reported study |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In pyridine; water; | Preparation Example 21 6-(4-Toluenesulfonylamino) isoquinoline In pyridine (30 ml) was dissolved <strong>[23687-26-5]6-aminoisoquinoline</strong> (3.348 g, Synthesis, 733 (1975), and 4-toluenesulfonyl chloride (5.13 g) was added thereto, followed by stirring at room temperature overnight. Water was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was recrystallized from ethanol, to give the title compound (5.958 g, 85%) as pale yellow crystals. 1H-NMR (DMSO-d6) delta (ppm): 2.28 (3H, s), 7.32 (2H, d, J=8.2 Hz), 7.40 (1H, dd, J=1.6, 9.2 Hz), 7.55 (1H, brs), 7.67 (1H, d, J=5.6 Hz), 7.74 (2H, d, J=8.2 Hz), 7.97 (1H, d, J=9.2 Hz), 8.36 (1H, d, J=5.6 Hz), 9.10 (1H, s). |
85% | In pyridine; water; | Production Example 21b 6-(4-Toluenesulfonylamino)isoquinoline 6-Aminoisoquinoline (3.348 g, Synthesis, 733 (1975)) was dissolved in pyridine (30 ml). To the mixture was added 4-toluenesulfonyl chloride (5.13 g), followed by stirring at room temperature overnight. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from ethanol, to give the title compound (5.958 g, 85%) as pale yellow crystals. 1H-NMR (DMSO-d6) delta (ppm): 2.28(3H, s), 7.32(2H, d, J = 8.2 Hz), 7.40(1H, dd, J = 1.6, 9.2 Hz), 7.55(1H, brs), 7.67(1H, d, J = 5.6 Hz), 7.74(2H, d, J = 8.2 Hz), 7.97(1H, d, J = 9.2 Hz), 8.36(1H, d, J = 5.6 Hz), 9.10(1H, s). |
85% | In pyridine; water; | PRODUCTION EXAMPLE 21b 6-(4-Toluenesulfonylamino)isoquinoline 6-Aminoisoquinoline (3.348 g, Synthesis, 733 (1975)) was dissolved in pyridine (30 ml). To the mixture was added 4-toluenesulfonyl chloride (5.13 g), followed by stirring at room temperature overnight. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from ethanol, to give the title compound (5.958 g, 85%) as pale yellow crystals. 1H-NMR (DMSO-d6) delta (ppm): 2.28(3H, s), 7.32(2H, d, J=8.2 Hz), 7.40(1H, dd, J=1.6, 9.2 Hz), 7.55(1H, brs), 7.67(1H, d, J=5.6 Hz), 7.74(2H, d, J=8.2 Hz), 7.97(1H, d, J=9.2 Hz), 8.36(1H, d, J=5.6 Hz), 9.10(1H, s). |
2.2 g | With pyridine; at 20℃; for 12h; | Isoquinolin-6-amine B24 (2.00 g, 13.87 mmol) was dissolved in pyridine (20 mL), and 4- methylbenzenesulfonyl chloride (3.17 g, 16.64 mmol) was added. The reaction mixture was stirred at 20C for 12 hours. LCMS showed the reaction was completed. To the reaction mixture was added water (30 mL) under good stirring, the mixture was stirred at 20C for 0.5 hour, pale yellow solid precipitated out. The mixture was filtered and the solid was collected and washed with water (5 mL) to give compound B25 (2.2g) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Prepared from 3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone and 1.1 equivalents of an oily mixture of 2-Boc-6-amino-1,2,3,4-tetrahydro-isoquinoline [prepared from <strong>[23687-26-5]6-amino-isoquinoline</strong>, melting point 218-220° C., by catalytic hydrogenation to obtain 6-amino-1,2,3,4-tetrahydro-isoquinoline (melting point: 69-71° C.) and subsequent reaction with 0.9 equivalents of di-tert.butyl pyrocarbonate (=(Boc)2 O)] in DMF by heating to 100° C. for 3.5 hours, pouring into water, filtering and washing the precipitate with water and EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-carbonyldiimidazole; In N-methyl-acetamide; dichloromethane; ethyl acetate; | EXAMPLE II N-(2-Hydroxyethyl)-N'-(isoquinolin-6-yl)-N-[4-[2-(methoxycarbonyl)ethyl]phenyl]-urea To 7.2 g of imidazole and 10.1 g of N,N'-carbonyldiimidazole in 100 ml of dimethylformamide are added dropwise, at a temperature of 0° to 10° C., 9.0 g of <strong>[23687-26-5]6-aminoisoquinoline</strong> in 70 ml of dimethylformamide. After 2 hours stirring at ambient temperature, 15.3 g of N-(2-hydroxyethyl)-4-[2-(methoxycarbonyl)ethyl]aniline in 20 ml of dimethylformamide are added dropwise and the mixture is stirred for 21/2 days at ambient temperature. The mixture is diluted with 750 ml of ethyl acetate and extracted twice with water and saturated saline solution. The organic phase is separated off, dried and evaporated down. The residue is purified by chromatography over a silica gel column using ethyl acetate/methylene chloride/methanol=70:30:10. Yield: 4.8 g (19percent of theory), Rf value: 0.48 (silica gel; methylene chloride/methanol/ethyl acetate=20:1:1) |