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Chemical Structure| 918488-41-2 Chemical Structure| 918488-41-2

Structure of 918488-41-2

Chemical Structure| 918488-41-2

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Product Details of [ 918488-41-2 ]

CAS No. :918488-41-2
Formula : C9H6ClNO
M.W : 179.60
SMILES Code : OC1=C(Cl)C2=C(C=NC=C2)C=C1
MDL No. :MFCD18822559
InChI Key :ALTPGTZNQQAMJI-UHFFFAOYSA-N
Pubchem ID :135742183

Safety of [ 918488-41-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 918488-41-2 ]

* 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 [ 918488-41-2 ]

[ 918488-41-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 7651-82-3 ]
  • [ 918488-41-2 ]
YieldReaction ConditionsOperation in experiment
89% 5-Chloroisoquinoline-6-ol (8)0.61 ml_ (1.02 g, 7.6 mmol) of sulfuryl chloride were added to a solution of 1.0 g (6,9 mmol) of compound 7 in 30 ml_ of dichloromethane. Three drops diethyl ether were EPO <DP n="37"/>added and the reaction was stirred at room temperature for 5 h. The solvents were removed by distillation and the remainder was treated with aqueous NaHCpsi3 solution.The precipitate was filtered, washed with water and dried to give 1.1 g (89percent) of compound 8 as a green-yellow solid.1H-NMR (de-DMSO): delta = 11.37 (1 H, s), 9.18 (1H, s), 8.50 (1H, d, J = 6 Hz)1 8.00 (1H, d, J= 8.8 Hz), 7.83 (1 H, J = 6 Hz), 7.44 (1 H, d, J = 8.7 Hz).MS: m/z = 180 (MH+).
89% 5-Chloroisoquinoline-6-ol (1); 0.61 mL (1.02 g, 7.6 mmol) of sulfuryl chloride were added to a solution of 1.0 g (6,9 mmol) of <strong>[7651-82-3]6-hydroxy-isoquinoline</strong> in 30 mL of dichloromethane. Three drops diethyl ether were added and the reaction was stirred at room temperature for 5 h. The solvents were removed by distillation and the remainder was treated with aqueous NaHCO3 solution. The precipitate was filtered, washed with water and dried to give 1.1 g (89percent) of 1 as a green-yellow solid.1H-NMR (d6-DMSO): delta = 11.37 (1 H, s), 9.18 (1 H, s), 8.50 (1 H, d, J = 6 Hz), 8.00 (1 H, d, J= 8.8 Hz), 7.83 (1 H1 J = 6 Hz), 7.44 (1 H, d, J = 8.7 Hz). MS: m/z = 180 (MH+).
11.4 mg With Escherichia coli BL21-CodonPlus (DE3)-RIL/pJZ54;Enzymatic reaction; General procedure: Thirty milligrams of 1 was fed into the IPTG induced fermentation broth of E. coli BL21-CodonPlus (DE3)-RIL/pJZ54 that expresses Rdc2. The culture was maintained at 28 °C with shaking at 250 rpm for 36 h. The ethyl acetate extract of the broth was fractionated on a Sephadex LH-20 (20 g) column eluted with methanol to give 14 fractions, 5 mL each. Fractions 3?6 were combined and further separated by reverse-phase HPLC (Eclipse XDB-C18 column, 5 mum, 4.6 × 150 mm) with isocratic elution of 25percent acetonitrile in H2O (each containing 0.1percent TFA) for 20 min at a flow rate of 1 mL/min to yield 8.5 mg of 1a. Similarly, 30 mg of 2 was also incubated with E. coli BL21-CodonPlus (DE3)-RIL/pJZ54 under the same conditions. The ethyl acetate extract was fractionated on a Diaion HP-20 (30 g) column eluted with a stepwise gradient of isopropanol?water (0:100, 20:80, 40:60, 60:40, 80:20, 100:0, each 250 mL) to give 6 fractions. Further separation of fraction 3 by reverse-phase HPLC with isocratic elution of 10percent acetonitrile in H2O (each containing 0.1percent TFA) over 20 min at a flow rate of 1 mL/min afforded 11.4 mg of 2a in pure form.
 

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