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[ CAS No. 17404-90-9 ] {[proInfo.proName]}

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Chemical Structure| 17404-90-9
Chemical Structure| 17404-90-9
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Product Details of [ 17404-90-9 ]

CAS No. :17404-90-9 MDL No. :MFCD01646204
Formula : C8H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :REUOCJLVDZPJEK-UHFFFAOYSA-N
M.W : 164.59 Pubchem ID :11194524
Synonyms :

Safety of [ 17404-90-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17404-90-9 ]

* 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.

  • Downstream synthetic route of [ 17404-90-9 ]

[ 17404-90-9 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 17404-90-9 ]
  • [ 17372-79-1 ]
YieldReaction ConditionsOperation in experiment
With ammonia; water; copper(II) sulfate
  • 2
  • toluene-4-sulfonic acid-[<i>N</i>'-(3-chloro-cinnolin-4-yl)-hydrazide] [ No CAS ]
  • [ 17404-90-9 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate
  • 3
  • [ 67-56-1 ]
  • [ 17404-90-9 ]
  • [ 17372-80-4 ]
YieldReaction ConditionsOperation in experiment
93% With sodium at 120℃; for 4h;
  • 4
  • [ 17404-90-9 ]
  • [ 100-52-7 ]
  • (3-chloro-4-cinnolinyl)phenylmethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane -75 deg C, 2 h; -75 deg C;
  • 5
  • [ 17404-90-9 ]
  • [ 75-07-0 ]
  • 1-(3-chloro-4-cinnolinyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane -75 deg C, 2 h; -75 deg C, 1 h;
  • 6
  • [ 17404-90-9 ]
  • 3,3'-dichloro-4,4'-bicinnolinyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With 2,2,6,6-tetramethylpiperidinyl-lithium; acetaldehyde In tetrahydrofuran; hexane -75 deg C, 0.5 h; -75 deg C, 1 h;
  • 7
  • [ 31777-46-5 ]
  • [ 17404-90-9 ]
YieldReaction ConditionsOperation in experiment
91% With trichlorophosphate for 240h; Heating;
72% With trichlorophosphate for 144h; Heating;
YieldReaction ConditionsOperation in experiment
Rk. m. LiAlH4 in Bzl. u. Ae. (Kochen) fuehrt zu 3-Chlor-1,4-dihydro-cinnolin;
Rk. m. H2 an Pd-Kohle (NEt3) fuehrt zu 1,4-Dihydro-cinnolin;
Rk. m. 30percentig. H2O2 u. Eg. bei 70grad fuehrt zu 3-Chlor-cinnolin-1-oxid;
YieldReaction ConditionsOperation in experiment
3-Amino-cinnolin, konz. HCl, Diazotierung bei 5grad, Ausbeute 27percent (neben Cinnolin-ol-(3) (30percent));
  • 10
  • [ 17404-90-9 ]
  • [ 75-66-1 ]
  • [ 766548-22-5 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium In tetrahydrofuran at 0 - 66℃; for 2.16667h;
  • 11
  • [ 17404-90-9 ]
  • [ 106-45-6 ]
  • [ 766548-23-6 ]
YieldReaction ConditionsOperation in experiment
87% With n-butyllithium In tetrahydrofuran at 0 - 66℃; for 2.16667h;
  • 12
  • [ 17404-90-9 ]
  • [ 766548-24-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / nBuLi / tetrahydrofuran / 2.17 h / 0 - 66 °C 2: 66 percent / m-CPBA / CH2Cl2 / 0.5 h / -10 °C
  • 13
  • [ 17404-90-9 ]
  • [ 766548-26-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 87 percent / nBuLi / tetrahydrofuran / 2.17 h / 0 - 66 °C 2: 76 percent / m-CPBA / CH2Cl2 / 0.5 h / -10 °C
  • 14
  • [ 17404-90-9 ]
  • [ 33844-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT
  • 15
  • [ 17404-90-9 ]
  • 8-iodo-3-methoxycinnoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h 4: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 5 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C
Multi-step reaction with 5 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT 4: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h 5: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C
  • 16
  • [ 17404-90-9 ]
  • [ 173415-24-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2
  • 17
  • [ 17404-90-9 ]
  • [ 173415-26-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 5 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h
Multi-step reaction with 4 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT 4: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h
  • 18
  • [ 17404-90-9 ]
  • 4,8-diiodo-3-methoxycinnoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 69 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2
  • 19
  • [ 17404-90-9 ]
  • 1-(3-methoxy-4-cinnolinyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 86 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 1 h
  • 20
  • [ 17404-90-9 ]
  • 3-methoxy-4-trimethylsilylcinnoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 63 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 0.5 h / -75 °C
  • 21
  • [ 17404-90-9 ]
  • 3-methoxy-4,8-ditrimethylsilylcinnoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 18 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 0.5 h / -75 °C
  • 22
  • [ 17404-90-9 ]
  • (3-methoxy-4-cinnolinyl)phenylmethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 91 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h
  • 23
  • [ 130111-80-7 ]
  • [ 17404-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: aqueous Na2CO3
  • 24
  • [ 17404-90-9 ]
  • [ 128-37-0 ]
  • [ 130579-43-0 ]
  • 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1,2,3,6-tetrahydro-1-acetyl-4-piperidinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 13 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1,2,3,6-tetrahydro-1-acetyl-4-piperidinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (17) EXAMPLE 13 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1,2,3,6-tetrahydro-1-acetyl-4-piperidinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (17) Chloronaphthyridine 16 (8.00 g, 25.7 mmol), and tributylvinylstannane 21 (12.0 g, 28.9 mmol) were dissolved in THF (130 ml) then flushed with nitrogen. Bis(triphenylphosphine)palladium dichloride (0.36 g, 0.5 mmol) and 2,6-di-t-butyl-4-methylphenol (~10 mg) were added to the reaction mixture. This orange solution was refluxed for 36 hours, then cooled and stirred at room temperature for 48 hours. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel with methylene chloride/methanol. The product fractions were recrystallized from THF to give 1.69 g of the title compound. MS-M+ =399, 356, 327, 82, 43 (base). NMR (CDCl3)-ppm 8.69 (s, 1H), 8.65 (dd, 1H, J=1, 15.5 Hz), 2.02-6.92 (m, 1H), 4.43-4.26 (m, H), 3.72 (apparent t, 1H), 3.67-3.61 (apparent t+m, 2H), 2.37-2.84 (m, 1H), 2.18 (m, 3H), 1.41 (5, 7 Hz), 1.37-1.03 (m, 4H).
  • 25
  • [ 17404-90-9 ]
  • C36H41BO2 [ No CAS ]
  • C38H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.6 g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 105℃; for 5h; 1 Reaction 1 Intermediate 1 (synthesized by the method described in WO2016194784A. 3.8 g), 3-chlorosinnoline (1.0 g), [Tetrakis (triphenylphosphine) palladium (0)] (0.15 g) in a 300 mL eggplant flask. ), 2M tripotassium phosphate aqueous solution (13m)L), toluene (26 mL) and ethanol (13 mL) were added, and the mixture was stirred in an oil bath at 105 ° C. for 5 hours. After cooling to room temperature, the aqueous phase was removed, the remaining liquid was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (neutral silica gel, ethyl acetate / hexane = 1/4). As a result, it was a pale yellow solid. As a result, 2.6 g of intermediate 2 was obtained.
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