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Chemical Structure| 630423-35-7 Chemical Structure| 630423-35-7

Structure of 630423-35-7

Chemical Structure| 630423-35-7

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Product Details of [ 630423-35-7 ]

CAS No. :630423-35-7
Formula : C10H8ClNO2
M.W : 209.63
SMILES Code : O=C1NC=C(OC)C2=C1C=C(Cl)C=C2
English Name :7-Chloro-4-methoxyisoquinolin-1(2H)-one
MDL No. :MFCD20922768

Safety of [ 630423-35-7 ]

Application In Synthesis of [ 630423-35-7 ]

* 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 [ 630423-35-7 ]

[ 630423-35-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 24188-74-7 ]
  • [ 630423-35-7 ]
YieldReaction ConditionsOperation in experiment
85% With methanesulfonic acid; [bis(acetoxy)iodo]benzene Inert atmosphere; Cooling with ice; Reflux; 3 To a 500 ml, 3-neck round-bottom flask (Flask A) equipped with overhead stirring, nitrogen inlet, heating mantle and temperature probe were charged the following reagents respectively: 1) starting isocarbostyril 2) Methanol (10 ml/g-bulk-LR) 3) Methanesulfonic acid Cooled Flask A via ice bath to 0° C.In a separate 250 ml, 3-neck round-bottom flask (Flask B) equipped with stir bar, nitrogen inlet, temperature probe and heating mantle was dissolved the oxidant in methanol (10 ml/g-bulk-LR) at 30° C.The completely homogeneous oxidant solution was then transferred to an addition funnel and added dropwise to the contents of Flask A, which resulted in a homogeneous solution.The ice bath was removed and the reaction was allowed to age at room temperature for 1 hour prior to heating to reflux.The reaction was then aged at reflux until complete conversion was observed (3-5 hours).Upon complete conversion the reaction volume was then reduced via atmospheric distillation (collected 92 ml distillate).The reaction was then cooled to room temperature and the resulting slurry was aged (at) rt overnight.The following morning, a total of 45 ml of H2O was slowly added dropwise via addition funnel as anti-solvent.The resulting slurry was aged 1 hour at room temperature prior to filtering.The resulting cake was washed with 100 ml 50:50 H2O/MeOH, then 2×100 ml H2O.The solids were dried on the frit under vacuum for several hours prior to being transferred to the vac oven were they continued to dry (at) 50° C. and 30 Hg over the weekend. Typical results range from 75-85% isolated yield with 97 LCAP (250 nm wavelength).
  • 2
  • [ 630423-35-7 ]
  • [ 630423-36-8 ]
YieldReaction ConditionsOperation in experiment
87% With trichlorophosphate In acetonitrile at 30℃; Inert atmosphere; Reflux; 4 To a 250 ml 3-neck round-bottom flask (Flask A) equipped with a stir bar, nitrogen inlet, temperature probe, heating mantle and reflux condenser were charged the following reagents respectively:1) starting isocarbostyril 2) acetonitrile 3) POCl3 (maintained temperature during addition below 30° C.) Began heating to reflux and followed conversion by LC analysis.In a separate, 3-neck round-bottom flask (Flask B) equipped with a stir bar, temperature probe, and cooling capabilities were charged the following reagents respectively:1) water-inverse quench 2) potassium phosphate, tribasic, N-hydrate Upon complete conversion the reaction solution was cooled to room temperature.The contents of Flask A were then transferred to Flask B maintaining the temperature below 10° C. during the inverse addition.Upon complete transfer, the resulting slurry was aged between 0-10° C. for 30 minutes.The following solvents were then charged to begin extractive workup:1) Tetrahydrofuran2) TolueneThe combined biphasic solution, Vmax=45 mL/g-bulk-LR, was stirred for 30 minutes as the temperature of the combined mixture increased to room temperature.Agitation was stopped and the layers were given time to separate.The layers were split and the aqueous layer was discarded,The organic layer was subjected to carbon treatment (10 wt % charge wrt Bulk-LR) for 1 hour with agitation.MgSO4 (1:1 charge wrt Bulk-LR) was then charged and the solution was again agitated for 1 hour.The solids were then filtered off and the resulting cake was washed with Tetrahydrofuran-Carbon cake wash.Organic layers were then combined and solvent-switched to n-Heptane in order to crystallize product from solution.After switching to n-Heptane, the resulting slurry is held at 50° C. with agitation for approximately 1 hour prior to cooling to 7° C.The resulting ‘cold’ slurry was then aged with agitation for an additional hour.The slurry was filtered and the solid washed with n-Heptane.Typical results range from 77-87% isolated yield; 98% LCAP (250 nm wavelength).
 

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