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Chemical Structure| 93258-88-9

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Product Details of [ 93258-88-9 ]

CAS No. :93258-88-9
Formula : C11H11NO3
M.W : 205.21
SMILES Code : O=C(C1=CC=CC2=C1CCNC2=O)OC
MDL No. :MFCD18250890
InChI Key :GSWJOSIENRJOBT-UHFFFAOYSA-N
Pubchem ID :69938631

Safety of [ 93258-88-9 ]

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 [ 93258-88-9 ]

* 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 [ 93258-88-9 ]

[ 93258-88-9 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 93258-88-9 ]
  • [ 26586-55-0 ]
  • [ 1262846-96-7 ]
YieldReaction ConditionsOperation in experiment
SS-B. 1-[4-(4-M&thyl-piρerazin-1-yi)-phenyi]-3-(1-oxo-1 ,2,3,4-tetrahyclro-isoquinolin-5-yl)- propane-1 ,3-dione.To a solution of compound 59-A (71.2 mg, 0.35 mmol) in anhydrous THF (2 mL) cooled in a bath of dry ice in acetone, is added a 1M solution of LHMDS in THF (0.7 mL, 0.7 mmol). A solution of compound 1-A (91 mg, 0.42 mmol) in tetrahydrofuran (1 mL) is added dropwise. The mixture is warmed to ambient temperature, then heated in an 8O0C oil bath and stirred for 2 hours, until conversion is judged to be complete. The mixture is cooled to ambient temperature and saturated aqueous ammonium chloride (5 mL) is added to quench the reaction. The aqueous phase is extracted with EtOAc (30 mL x 2). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by flash column chromatography with 0 - 10% methanol in dichloromethane to afford product as a yellow solid. MS(ESI) m/z = 392.2 (M+1).
  • 3
  • [ 67-56-1 ]
  • [ 1109230-25-2 ]
  • [ 201230-82-2 ]
  • [ 93258-88-9 ]
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In N,N-dimethyl-formamide; at 22.0℃; under 760.051 Torr; for 156.0h; Pd(dppf)Cb DCM (285 mg, 0.35 mmol) was added to a solution of 5-bromo- 3,4-dihydro-2H-isoquinolin-l-one (395 mg, 1.75 mmol) and TEA (1.22 mL, 8.74 mmol) in DMF (6.00 mL) at 22 C. The mixture was evacuated and refilled with CO for 3 cycles. MeOH (3.08 mL) was added, and the mixture was heated to 85 C under a CO atmosphere (1 atm) for 16 h. The mixture was diluted with EA (25 mL) and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was diluted with EA (100 mL) and LhO (100 mL). The aq. phase was extracted with EA (3 x 25.0 mL). The combined organic layers were washed with brine (50 mL), dried (NaiSO^, filtered, and concentrated. The residue was purified by S1O2 chromatography (hexanes and EA) to provide 285 mg (80%) of methyl l-oxo-l,2,3,4-tetrahydroisoquinoline-5-carboxylate (INT 58-1). LCMS-ESI (m/z) calculated for C11H11NO3: 205.07; found 205.74 (M+H)+, tR = 1.82 min (Method 13). NMR (400 MHz, CDCh) d 8.30 (dd, J = 7.7, 1.5 Hz, 1H), 8.09 (dd, J = 7.8, 1.5 Hz, 1H), 7.42 (dd, J = 7.8 Hz, 1H), 5.95 (s, 1H), 3.92 (s, 3H), 3.58 - 3.52 (m, 2H), 3.49 - 3.40 (m, 2H).
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In N,N-dimethyl-formamide; at 85.0℃; under 760.051 Torr; for 16.0h; To a stirred solution of 5-bromo-3,4-dihydro-2H-isoquinolin-1-one (395 mg, 1.0 equiv., 1.75 mmol) and Et3N (1.22 mL, 5.0 equiv., 8.74 mmol) in DMF (6 mL) was added Pd(dppf)Cl2·DCM (285 mg, 0.2 equiv., 0.35 mmol). The mixture was evacuated and refilled with CO for 3 cycles. MeOH (3.08 mL, 43.42 equiv., 76.00 mmol) was added, and the mixture was heated to 85 C under a CO atmosphere (1 atm) for 16 h. The mixture was diluted with EA (25 mL) and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was diluted with EA (100 mL) and water (100 mL). The aqueous phase was extracted with EA (3 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash SiO2 chromatography (0-100% EA/hexanes) to afford 285 mg (80 %) of methyl 1-oxo-1,2,3,4-tetrahydroisoquinoline-5- carboxylate (INT 6-A). MS-ESI calculated for C11H11NO3: 205.07; found 205.74 [M]+, tR = 1.82 min (Method 5). 1H NMR (400 MHz, CDC13) δ 8.30 (dd, J = 7.7, 1.5 Hz, 1H), 8.09 (dd, J = 7.8, 1.5 Hz, 1H), 7.42 (dd, J = 7.8 Hz, 1H), 5.95 (s, 1H), 3.92 (s, 3H), 3.58 - 3.52 (m, 2H), 3.49 - 3.40 (m, 2H).
  • 4
  • [ 93258-88-9 ]
  • 5-(hydroxymethyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With lithium borohydride; In tetrahydrofuran; at 22.0℃; for 20.0h;Inert atmosphere; L1BH4 (2 M in THF, 2.66 mL, 5.32 mmol) was added to a solution of INT 58-1 (182 mg, 0.887 mmol) in THF (5.00 mL) at 22 C under N2. The mixture was stirred at 22 C for 20 h. The mixture was diluted with sat. aq. NH4CI (10 mL). The aq. phase was extracted with EA (3 x 20 mL), and the combined organic phases were washed with brine (50 mL), dried (NaiSCL), filtered, and concentrated to provide 88 mg (56%) of 5- (hydroxymethyl)-3,4-dihydroisoquinolin-l(2H)-one (INT 58-2) as an oil. LCMS-ESI (m/z) calculated for C10H11NO2: 177.08; found 178.13 (M+H)+, tR = 1.39 min (Method 13). NMR (500 MHz, CDCh) 5 8.07 (dd, J = 7.8, 1.4 Hz, 1H), 7.52 (dd, J = 7.6, 1.4 Hz, 1H), 7.36 (t, J = 7.7 Hz, 1H), 5.95 (s, 1H), 4.75 (s, 2H), 3.57 (td, J = 6.7, 2.9 Hz, 2H), 3.07 (t, J = 6.6 Hz, 2H), 1.72 (s, 1H).
56% With lithium borohydride; In tetrahydrofuran; at 20.0℃; for 20.0h; To a stirred solution of INT 6-A (182 mg, 1.0 equiv., 0.89 mmol) in THF (5 mL) at room temperature under nitrogen was added LiBH4 (2 M in THF, 2.66 mL, 6.0 equiv., 5.32 mmol). The resulting mixture was stirred at room temperature for 20 hours. The mixture was diluted with sat. aq. NH4Cl (10 mL). The aq. phase was extracted with EA (3 x 20 mL), and the combined organic phases were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo to afford 88 mg (56%) of 5-(hydroxymethyl)- 3,4-dihydroisoquinolin-1(2H)-one (INT 6-B). MS-ESI (m/z) calculated for C10H11NO2: 177.08; found 178.13 [M+H]+, tR = 1.39 min (Method 5). 1H NMR (500 MHz, CDC13) δ 8.07 (dd, J = 7.8, 1.4 Hz, 1H), 7.52 (dd, J = 7.6, 1.4 Hz, 1H), 7.36 (t, J = 7.7 Hz, 1H), 5.95 (s, 1H), 4.75 (s, 2H), 3.57 (td, J = 6.7, 2.9 Hz, 2H), 3.07 (t, J = 6.6 Hz, 2H), 1.72 (s, 1H).
  • 5
  • [ 93258-88-9 ]
  • 5-((2-chloro-4-(trifluoromethyl)phenoxy)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • 6
  • [ 93258-88-9 ]
  • 5-((2-chloro-4-(trifluoromethyl)phenoxy)methyl)-2-methyl-3,4-dihydroi soquinolin-1(2H)-one [ No CAS ]
 

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