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CAS No. : | 68050-37-3 | MDL No. : | MFCD16659152 |
Formula : | C9H7ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LFNYFPRSHXRDDH-UHFFFAOYSA-N |
M.W : | 178.62 | Pubchem ID : | 14067426 |
Synonyms : |
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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: |
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* 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 |
---|---|---|
With methyloxirane; In 1,2-dimethoxyethane; ethanol; | EXAMPLE 29 ethyl 6-chloroimidazo-[1,2-a]-quinoline-2-carboxylate 140 mg of <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> were dissolved in 2.5 ml of dimethoxyethane and then a mixture of 170 mg of ethyl bromopyruvate and 30 mg of propylene oxide was added. The mixture was stirred at room temperature for 2 hours and 2 ml of ether were added. Then, the mixture was cooled in ice and the precipitated quaternary salt was filtered off, was dissolved in 5 ml of ethanol and the solution was heated at reflux for 2 hours. Then, the solvent was removed under vacuum and the residue was partitioned between sodium bicarbonate solution and chloroform. The chloroform solution was dried over magnesium sulfate and was evaporated to dryness. The residue was chromatographed over silica with chloroform as eluent and the purified product was recrystallized from ethyl acetate/petroleum ether to obtain colorless needles of ethyl 6-chloroimidazo-[1,2-a]-quinoline-2-carboxylate melting at 193-194 C. I.R. (KBr Disc): 3145 cm-1 (C--H1 stretch) 1707 cm-1 (Ester C=O) Analysis: C14 H11 N2 Cl O2. Calculated: %C 61.21; %H 4.04; %N 10.20; Found: C 61.13; H 4.05; N 10.07 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 26 N-(5-Chloroquinolin-2-yl)-4-sulfamoylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Preparation Example 2) and 4-sulfamoylbenzenesulfonyl chloride by the procedure of Example 1. 1H-NMR (CDCl3) delta (ppm): 7.42-7.49 (3H, m), 7.58 (1H, t, J=8.0 Hz), 8.00-8.12 (4H, m,), 8.39 (1H, d, J=9.3 Hz). | ||
Synthetic Example 26b N-(5-Chloroquinoline-2-yl)-4-sulfamoylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-sulfamoylbenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 7.42-7.49(3H, m,), 7.58(1H, t,J=8.0Hz), 8.00-8.12(4H,m,) 8.39(1H, d, J=9.3Hz). | ||
SYNTHETIC EXAMPLE 26b N-(5-Chloroquinoline-2-yl)-4-sulfamoylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-sulfamoylbenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 7.42-7.49 (3H, m,), 7.58(1H, t, J=8.0 Hz), 8.00-8.12(4H, m,) 8.39(1H, d, J=9.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 27 N-(5-Chloroquinolin-2-yl)-4-(N-ethylsulfamoyl)benzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Preparation Example 2) and 4-(N-ethylsulfamoyl)benzenesulfonyl chloride by the procedure of Example 1. 1H-NMR (CDCl3) delta (ppm): 1.14 (3H, t, J=7.5 Hz), 3.01-3.09 (2H, m), 7.08 (1H, d, J=9.5 Hz), 7.42 (1H, dd, J=7.6 Hz, 1.3 Hz), 7.49 (1H, t, J=7.6 Hz),7.65 (1H, dd, J=7.6 Hz, 1.3 Hz), 7.96 (2H, d, J=8.7 Hz), 8.10 (2H, d, J=8.7 Hz), 8.31 (1H, d, J=9.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 25 N-(5-Chloroquinolin-2-yl)-4-methylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Preparation Example 2) and 4-toluenesulfonyl chloride by the procedure of Example 1. 1H-NMR (CDCl3) delta (ppm): 2.41 (3H, s), 6.98 (1H, d, J=9.3 Hz), 7.28 (2H, d, J=8.2 Hz), 7.35 (1H, d, J=7.9 Hz), 7.41 (1H, d, J=7.9 Hz), 7.53 (1H, t, J=7.9 Hz), 7.88 (2H, d, J=8.2 Hz), 8.26 (1H, d, J=9.3 Hz) | ||
Synthetic Example 25b N-(5-Chloroquinoline-2-yl)-4-methylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-toluenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 2.41(3H, s), 6.98(1H, d, J=9.3Hz), 7.28(2H, d, J=8.2Hz), 7.35(1H, d, J=7.9Hz), 7.41(1H, d, J=7.9Hz), 7.53(1H, t, J=7.9Hz), 7.88(2H, d, J=8.2Hz), 8.26(1H, d, J=9.3Hz). | ||
SYNTHETIC EXAMPLE 25b N-(5-Chloroquinoline-2-yl) -4-methylbenzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-toluenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 2.41(3H, s), 6.98(1H, d, J=9.3 Hz), 7.28(2H, d, J=8.2 Hz), 7.35(1H, d, J=7.9 Hz), 7.41(1H, d, J=7.9 Hz), 7.53(1H, t, J=7.9 Hz), 7.88(2H, d, J=8.2 Hz), 8.26(1H, d, J=9.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In water; | Example 20 4-Chloro-N-(5-chloroquinolin-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Preparation Example 2) at room temperature. After stirring at room temperature for 3 days, water was added thereto and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR (CDCl3) delta (ppm): 6.96 (1H, d, J=9.7 Hz), 7.34 (1H, d, J=8.4 Hz), 7.42-7.48 (3H, m), 7.54 (1H, t, J=8.4 Hz), 7.94 (2H, d, J=6.3 Hz), 8.29 (1H, d, J=9.7 Hz). | |
With pyridine; In water; | Synthetic Example 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, theresulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta(ppm): 6.96(1H,d,J=9.7Hz), 7.34(1H,d,J=8.4Hz), 7.42-7.48(3H,m), 7.54(1H,t,J=8.4Hz),7.94(2H,d,J=6.3Hz), 8.29(1H,d,J=9.7Hz). | |
With pyridine; In water; | SYNTHETIC EXAMPLE 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.7 Hz), 7.34(1H, d, J=8.4 Hz), 7.42-7.48(3H, m), 7.54(1H, t, J=8.4 Hz),7.94(2H, d, J=6.3 Hz), 8.29(1H, d, J=9.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 24 4-Cyano-N-(5-chloroquinolin-2-yl)-benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Preparation Example 2) and 4-cyanobenzenesulfonyl chloride by the procedure of Example 1. 1H-NMR (CDCl3) delta (ppm): 6.96 (1H, d, J=9.5 Hz), 7.35 (1H, d, J=8.7 Hz), 7.45 (1H, d, J=8.7 Hz), 7.57 (1H, t, J=8.7 Hz), 7.78 (2H, d, J=8.9 Hz), 8.10 (2H, d, J=8.9 Hz), 8.33 (1H, d, J=9.5 Hz). | ||
Synthetic Example 24b 4-Cyano-N-(5-chloroquinoline-2-yl)-benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Production Example 2b) and 4-cyanobenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.5Hz), 7.35(1H, d,J=8.7Hz), 7.45(1H, d, J=8.7Hz), 7.57(1H, t J=8.7Hz), 7.78(2H, d, J=8.9Hz), 8.10(2H, d, J=8.9Hz), 8.33(1H, d, J=9.5Hz). | ||
SYNTHETIC EXAMPLE 24b 4-Cyano-N-(5-chloroquinoline-2-yl) -benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Production Example 2b) and 4-cyanobenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.5 Hz), 7.35(1H, d, J=8.7 Hz), 7.45(1H, d, J=8.7 Hz), 7.57(1H, tJ=8.7 Hz), 7.78(2H, d, J=8.9 Hz), 8.10(2H, d, J=8.9 Hz), 8.33(1H, d, J=9.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation Example 2 2-Amino-5-chloroquinoline The title compound was obtained from 2-chloro-6-nitrobenzaldehyde in the same manner as in Preparation Example 1. 1H-NMR (CDCl3) delta (ppm): 5.25 (2H, bs), 6.80 (1H, d, J=9.7 Hz), 7.32 (1H, dd, J=7.5 Hz, 1.5 Hz), 7.46 (1H, t, J=7.5 Hz), 7.57 (1H, m), 8.30 (1H, d, J-=9.7 Hz, 1.0 Hz). | ||
Production Example 2b 2-Amino-5-chloroquinoline The title compound was obtained from 2-chloro-6-nitrobenzaldehyde in the same manner as in Production Example 1b. 1H-NMR(CDCl3) delta (ppm): 5.25(2H,bs), 6.80(1H,d,J=9.7Hz), 7.32(1H,dd,J=7.5Hz,1.5Hz), 7.46(1H,t,J=7.5Hz), 7.57(1H,m), 8.30(1H,d,J=9.7Hz,1.0Hz). | ||
PRODUCTION EXAMPLE 2b 2-Amino-5-chloroquinoline The title compound was obtained from 2-chloro-6-nitrobenzaldehyde in the same manner as in Production Example 1b. 1H-NMR(CDCl3) delta (ppm): 5.25(2H, bs), 6.80(1H, d, J=9.7 Hz), 7.32(1H, dd, J=7.5 Hz, 1.5 Hz), 7.46(1H, t, J=7.5 Hz), 7.57(1H, m), 8.30(1H, d, J=9.7 Hz, 1.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthetic Example 27b N-(5-Bromoquinoline-2-yl)-4-(N-ethylsulfamoyl)benzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-(N-ethylsulfamoyl)benzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 1.14 (3H,t,J-7.5Hz), 3.01-3.09(2H,m), 7.08(1H,d, J=9.5Hz), 7.42(1H,dd,J=7.6Hz,1.3Hz), 7.49(1H,t,J=7.6Hz),7.65(1H,dd,J= 7.6Hz,1.3Hz), 7.96(2H,d,J=8.7Hz), 8.10(2H,d,J=8.7Hz), 8.31(1H,d,J=9.5Hz). | ||
SYNTHETIC EXAMPLE 27b N-(5-Bromoquinoline-2-yl)-4-(N-ethylsulfamoyl)benzenesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 4-(N-ethylsulfamoyl)benzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 1.14(3H, t, J=7.5 Hz), 3.01-3.09(2H, m), 7.08(1H, d, J=9.5 Hz), 7.42(1H, dd, J=7.6 Hz, 1.3 Hz), 7.49(1H, t, J=7.6 Hz), 7.65(1H, dd, J=7.6 Hz,1.3Hz), 7.96(2H, d, J=8.7 Hz), 8.10(2H, d, J=8.7 Hz), 8.31(1H, d, J=9.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthetic Example 22b N-(5-Chloroquinoline-2-yl)-6-ethyl-3-pyridinesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 6-ethyl-3-pyridinesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 1.32(3H, t, J=8.3Hz), 2.89(2H, q, J=8.3Hz), 6.97(1H, d, J=9.4Hz), 7.29(1H, d, J=8.0Hz), 7.35(1H, d, J=8.0Hz),7.44(1H, d, J=8.0Hz), 7.56(1H, t, J=8.0Hz), 8.18(1H, dd, J=8.0Hz, 2.6Hz), 8.30(1H, d, J=9.4Hz), 9.10(1H,d, J=2.6Hz). | ||
SYNTHETIC EXAMPLE 22b N-(5-Chloroquinoline-2-yl)-6-ethyl-3-pyridinesulfonamide The title compound was obtained from <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (Production Example 2b) and 6-ethyl-3-pyridinesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 1.32(3H, t, J=8.3 Hz), 2.89(2H, q, J=8.3 Hz), 6.97(1H, d, J=9.4 Hz), 7.29(1H, d, J=8.0 Hz), 7.35(1H, d, J=8.0 Hz), 7.44(1H, d, J=8.0 Hz), 7.56(1H, t, J=8.0 Hz), 8.18(1H, dd, J=8.0 Hz, 2.6Hz), 8.30(1H, d, J=9.4 Hz), 9.10(1H, d, J=2.6 Hz). |