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[ CAS No. 1532-72-5 ]

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Chemical Structure| 1532-72-5
Chemical Structure| 1532-72-5
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CAS No. :1532-72-5 MDL No. :MFCD00006903
Formula : C9H7NO Boiling Point : 388.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :145.16 g/mol Pubchem ID :290378
Synonyms :

Safety of [ 1532-72-5 ]

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:

Application In Synthesis of [ 1532-72-5 ]

  • Upstream synthesis route of [ 1532-72-5 ]
  • Downstream synthetic route of [ 1532-72-5 ]

[ 1532-72-5 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1532-72-5 ]
  • [ 19493-44-8 ]
YieldReaction ConditionsOperation in experiment
85% at 105℃; Cooling with ice Phosphorus oxychloride (200 ml_) was added dropwise under ice-cold condition to isoquinolin-/V-oxide (20.0 g). The reaction mixture was then heated to reflux at 105 °C overnight. Phosphorus oxychloride was evaporated under reduced pressure, then the residue was quenched with ice and extracted with dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated. The crude was purified by column chromatography on silica gel using ethylacetate and petroleum ether as eluent (21.0 g; 85percent). 1H NMR (400 MHz, DMSO-d6): δ 8.25-8.31 (m, 2H), 8.08 (d, J= 8.0 Hz, 1 H), 7.88-7.91 (m, 2H), 7.80-7.84 (m, 1 H). MS (ESI+): 164.0, HPLC (Method A) Rt 8.29min; HPLC purity 96.0 percent
69% With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1M) at 0 °C is added POCl3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7~8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (80:1) as eluent.
44.9% With trichlorophosphate In chloroform at 15 - 20℃; for 3 h; Heating / reflux 69.3 g of isoquinoline N-oxide (448 mmole) available from Tokyo Kasei Co. and 225 ml of chloroform were introduced into a 1L-three-neck flask to dissolve therein. Then, 219.6 g (1432 mmole) of phosphorous oxychloride was slowly dropped therein and stirred under ice-cooling while maintaining the inner temperature at 15 to 20°C. Thereafter, the temperature was raised, and the mixture was stirred under reflux for 3 hours. The reaction product was left to cool to room temperature, followed by pouring the resultant into an ice water. The mixture was extracted with ethyl acetate, an organic layer was washed with water till it showed neutral pH, and then the solvent was removed under reduced pressure. The residue was purified using silica gel column chromatography (eluent: chloroform/hexane: 5/1), to yield 35.5 g of a white crystal of 1- chloroisoquinoline (44. 9percent yield).
Reference: [1] Organic Letters, 2015, vol. 17, # 12, p. 2948 - 2951
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[3] Patent: WO2013/92979, 2013, A1, . Location in patent: Page/Page column 54
[4] Journal of Organic Chemistry, 1998, vol. 63, # 20, p. 6886 - 6890
[5] Tetrahedron: Asymmetry, 1993, vol. 4, # 4, p. 743 - 756
[6] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1890 - 1896
[7] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5341 - 5348
[8] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132
[9] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1589 - 1592
[10] Patent: WO2004/60876, 2004, A1, . Location in patent: Page 7-8
[11] Pharmaceutical Bulletin, 1954, vol. 2, p. 111,113
[12] Dalton Transactions, 2005, # 9, p. 1583 - 1590
[13] Organic Letters, 2016, vol. 18, # 9, p. 1956 - 1959
  • 2
  • [ 1532-72-5 ]
  • [ 116833-54-6 ]
  • [ 1532-94-1 ]
  • [ 19493-44-8 ]
  • [ 491-30-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 45, p. 7247 - 7250
  • 3
  • [ 1532-72-5 ]
  • [ 2439-04-5 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014
[3] Yakugaku Zasshi, 1953, vol. 73, p. 666[4] Chem.Abstr., 1954, p. 7014
[5] Yakugaku Zasshi, 1953, vol. 73, p. 666[6] Chem.Abstr., 1954, p. 7014
  • 4
  • [ 1532-72-5 ]
  • [ 23687-27-6 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 2521,2527
  • 5
  • [ 119-65-3 ]
  • [ 1532-72-5 ]
YieldReaction ConditionsOperation in experiment
96% With dihydrogen peroxide In water for 0.25 h; Sonication In a 50 mL round bottom flask, quinoline 1.29 g, hydrogen peroxide (35percent mass fraction) 1.1 g, 5percent by mass were added in order.Number of perfluorosulfonic acid resin, 10 ml of water as a solvent, and the resulting mixture reacted for 15 minutes in a 30 W/20 KHz ultrasonic reactorbell. The resin catalyst in the reaction system is removed by filtration, the water in the reaction solvent is removed under reduced pressure, and finally recrystallized to obtain the correspondingQuinoline nitrogen oxide 1.39 g, yield 96percent.
90% With dihydrogen peroxide In ethanol; water at 20℃; for 24 h; {Mo132} 100 mg,Isoquinoline 1 mmol,30percent Hydrogen peroxide 5 mmol,Ethanol 2 ml and water 3 ml were mixed and stirred at room temperature,After the reaction for 24 hours, it was extracted with dichloromethane and then purified by distillation with organic phase dichloromethane to give the isoquinoline pyridine nitroxide in a yield of 90percent.
89.6% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18 h; To a stirred solution of isoquinoline (43-1) (2 g, 15.4 mmol) in dichloromethane (50 mL) at 0°C, was added mCPBA (3.77 g, 16.9 mmol) portionwise and the reaction mixture was stirred at RT for 18 h. After consumption of starting material as evident from TLC, the reaction mixture was quenched with a saturated solution of sodium sulphite, the organic layer was separated and washed with a saturated solution of sodium carbonate, brine, dried over anhydrous sodium sulphate, and concentrated under reduced pressure to afford isoquinoline 2-oxide (43-2) (2.00 g, 13.7 mmol, 89.6 percent) as a white gummy solid. 1H NMR (400 MHz, DMSO-d6) δ 8.75 (s, 1H), 8.12 (d, J = 6 Hz, 1H), 7.85-7.58 (m, 4H).
88% With K8[α-BHW11O39]*13H2O; dihydrogen peroxide In water at 65℃; for 6 h; Green chemistry General procedure: Catalyst (0.03 mmol), H2O (3 ml), substrate (4 mmol), and H2O2 (20 mmol, 30percent aq.) were charged in the reaction flask, which was first bathed in cold water (about 283 K). The mixture was then stirred at room temperature for 16–24 h. The reaction was detected by thin-layer chromatography (TLC). After the reaction, the system was concentrated by evaporation, and the catalyst precipitated from the mixture after the addition of anhydrous ethyl alcohol. The recovered catalyst, obtained by filtration, was washed with anhydrous ethyl alcohol and diethyl ether and then used for the next oxidation after drying. The filtrate was extracted with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4, and the pure products were obtained by evaporation or column chromatography. The products were analyzed by 1H NMR and 13C NMR.
86.8% at 40℃; for 24 h; step one,Tungsten-loaded titanium dioxide is used as a catalyst.50g isoquinoline,40mL 30percent hydrogen peroxide solution,5g of the catalyst prepared in step (a) was added to the three-necked flask;Step two,The mixture prepared in step 1 is stirred and reacted at 40° C. for 24 hours.After the reaction liquid is naturally cooled to room temperature, it is filtered, washed and concentrated.After the filtrate is concentrated, the yield of isoquinoline nitrogen oxide product is 86.8percent.The purity by HPLC was 94.8percent.
78% With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane In acetonitrile at 20℃; for 0.216667 h; General procedure: To a solution of pyridine derivative 1 or tertiary amine 2(1 mmol) in acetonitrile (5 mL) was added 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane (1 g, 3 mmol). The resulting mixture was stirred at room temperature for an appropriate time (Table 2). After completion of the reaction as monitored by TLC, the reaction mixture was diluted with toluene (10 mL) and water (6 mL). The aqueous layer which contained the product was separated from theorganic layer and evaporated under reduced pressure toleave the product. The products were characterized on the basis of their melting points, elemental analysis and IR, 1HNMR and 13C NMR spectral analysis.
75% With dihydrogen peroxide; sodium hydrogencarbonate; trichloroacetonitrile In tetrahydrofuran; water at 0 - 25℃; for 12 h; General procedure: To a stirred solution of amine (1 mmol), trichloroacetonitrile (2 mmol), and NaHCO3 (0.5 mmol) inTHF (2 mL) was added an aqueous solution of 30percent (w/w) hydrogen peroxide(2 mmol, 0.2 mL) at 0 °C. The temperature was increased to 25 °C and the reaction continued. After completion of the reaction (monitored by TLC), the solvent was evaporated and MeCN (2 mL) was added. The mixture was cooled to 0 °C and filtered to remove the trichloroacetamide by-product. The filtrate was then concentrated under reduced pressure and purified by column chromatography. The products were identified by comparing their physical and spectral data with those of authentic samples reported in the literature.
64% With peracetic acid In ethyl acetate at 20℃; Add isoquinoline (500.00 g, 3.75 moles) and ethyl acetate (7.60 L, 77.62 moles) to a 22 L three- necked round-bottom flask in a water bath equipped with overhead stirrer, thermocoupler, nitrogen inlet/outlet, and addition funnel. Stir to dissolve. At room temperature add peracetic acid (1.25 L, 5.94 moles) dropwise over 0.5 ours. Stir at room temperature overnight. Chill the reaction flask in an ice-water bath, then quench the reaction by dropwise addition of dimethyl sulfide (525.00 mL, 7.14 moles) over 45 minutes. Stir overnight while warming to room temperature. Test the reaction mixture for peroxide.Combine two lots of the reaction mixture. Transfer the reaction mixtures to a 50 L separatory funnel and add water (2.00 L, 111.02 moles) and dichloromethane (12.00 L, 187.21 moles). Add sodium carbonate (2.07 kg, 19.53 moles) in portions, then separate layers. Extract the aqueous layer with dichloromethane ( 3 x 4 L), combine the organic layers and dry over sodium sulfate. Filter and remove solvent under reduced pressure to afford a crude dark red oil/liquid.Add ethyl acetate (8.00 L, 81.76 moles) to the crude dark red oil/liquid, then stir under reduced pressure until 6.8 L of ethyl acetate are removed. Filter the precipitated solid, wash with cold ethyl acetate (750.00 mL, 7.66 moles), then heptane (800.00 mL, 5.46 moles) wash. Dry the solid to afford isoquinoline- 2-oxide, 714.20 g (64percent) as a fine sand-like solid.As an alternative work-up, prior to the heptane wash, remove IL of solvent from the filtrate. Allow the filtrate to stand overnight. Filter the solid and wash with cold ethyl acetate (500.00 mL, 5.11 moles), followed by a heptane (500.00 mL, 3.41 moles) wash. The solid was dried to afford isoquinoline-2-oxide, 110.10 g (10percent) as a fine sand-like solid - cropNo.2 (total yield 74percent).

Reference: [1] Organic Letters, 2018, vol. 20, # 8, p. 2346 - 2350
[2] Heterocyclic Communications, 2007, vol. 13, # 1, p. 25 - 28
[3] Chemistry - A European Journal, 2014, vol. 20, # 2, p. 559 - 563
[4] Patent: CN108003098, 2018, A, . Location in patent: Paragraph 0085; 0086; 0087
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 3291 - 3306
[6] Synthesis, 1997, # 12, p. 1387 - 1388
[7] Journal of Organic Chemistry, 1998, vol. 63, # 5, p. 1740 - 1741
[8] New Journal of Chemistry, 2013, vol. 37, # 9, p. 2614 - 2618
[9] ChemCatChem, 2015, vol. 7, # 23, p. 3903 - 3910
[10] RSC Advances, 2015, vol. 5, # 46, p. 36809 - 36812
[11] Patent: CN104628636, 2017, B, . Location in patent: Paragraph 0024; 0025
[12] Patent: WO2017/197046, 2017, A1, . Location in patent: Page/Page column 342; 343
[13] Synthetic Communications, 2014, vol. 44, # 1, p. 150 - 160
[14] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825
[15] Chemical Communications, 2016, vol. 52, # 9, p. 1831 - 1834
[16] Patent: CN104974088, 2017, B, . Location in patent: Paragraph 0139; 0143; 0144; 0145
[17] Synthetic Communications, 2004, vol. 34, # 2, p. 247 - 253
[18] Journal of the Iranian Chemical Society, 2016, vol. 13, # 4, p. 645 - 651
[19] Organic and Biomolecular Chemistry, 2014, vol. 12, # 19, p. 3026 - 3036
[20] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1589 - 1592
[21] Tetrahedron, 1994, vol. 50, # 42, p. 12185 - 12200
[22] Tetrahedron Letters, 2014, vol. 55, # 15, p. 2513 - 2516
[23] Journal of Fluorine Chemistry, 1996, vol. 80, # 1, p. 31 - 34
[24] Patent: WO2007/53346, 2007, A1, . Location in patent: Page/Page column 20
[25] Chemical Communications, 2002, # 10, p. 1040 - 1041
[26] Angewandte Chemie - International Edition, 2015, vol. 54, # 51, p. 15545 - 15549[27] Angew. Chem., 2015, vol. 127, # 51, p. 15766 - 15770,5
[28] Tetrahedron, 1989, vol. 45, # 11, p. 3299 - 3306
[29] Chemical Communications (Cambridge, United Kingdom), 2000, # 17, p. 1577 - 1578
[30] Chemische Berichte, 1926, vol. 59, p. 1850[31] Chemische Berichte, 1933, vol. 66, p. 986 Anm. 7
[32] Journal of Organic Chemistry, 1956, vol. 21, p. 1337,1340
[33] Organic Mass Spectrometry, 1991, vol. 26, # 4, p. 247 - 249
[34] Tetrahedron, 1981, vol. 37, p. 1871 - 1873
[35] Tetrahedron, 1997, vol. 53, # 46, p. 15877 - 15888
[36] Synthesis, 1999, # SPEC. ISS., p. 1427 - 1430
[37] Patent: EP705821, 1996, A1,
[38] Angewandte Chemie - International Edition, 2007, vol. 46, # 46, p. 8872 - 8874
[39] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4441 - 4447
[40] Journal of the American Chemical Society, 2009, vol. 131, # 39, p. 13888 - 13889
[41] Journal of Molecular Catalysis A: Chemical, 2011, vol. 337, # 1-2, p. 45 - 51
[42] Green Chemistry, 2011, vol. 13, # 6, p. 1486 - 1489
[43] Patent: WO2011/79114, 2011, A1, . Location in patent: Page/Page column 108
[44] Polyhedron, 2011, vol. 30, # 14, p. 2391 - 2399
[45] Polyhedron, 2012, vol. 33, # 1, p. 9 - 12
[46] Organic Letters, 2013, vol. 15, # 6, p. 1270 - 1273
[47] Patent: WO2013/92979, 2013, A1, . Location in patent: Page/Page column 53
[48] Organic and Biomolecular Chemistry, 2015, vol. 13, # 11, p. 3207 - 3210
[49] Organic and Biomolecular Chemistry, 2015, vol. 13, # 46, p. 11184 - 11188
[50] European Journal of Organic Chemistry, 2015, vol. 2015, # 10, p. 2133 - 2137
[51] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[52] Green Chemistry, 2016, vol. 18, # 12, p. 3518 - 3521
[53] Journal of Organic Chemistry, 2016, vol. 81, # 14, p. 5886 - 5894
[54] Chemical Communications, 2016, vol. 52, # 65, p. 10028 - 10031
[55] Organic Letters, 2016, vol. 18, # 16, p. 4144 - 4147
[56] Chemistry - A European Journal, 2016, vol. 22, # 39, p. 13826 - 13830
[57] New Journal of Chemistry, 2016, vol. 40, # 12, p. 10227 - 10232
[58] European Journal of Organic Chemistry, 2017, vol. 2017, # 5, p. 1025 - 1032
[59] Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3165 - 3169
[60] Journal of Organic Chemistry, 2017, vol. 82, # 17, p. 8933 - 8942
[61] Advanced Synthesis and Catalysis, 2018, vol. 360, # 5, p. 905 - 910
[62] Tetrahedron Letters, 2018, vol. 59, # 18, p. 1752 - 1756
  • 6
  • [ 91-21-4 ]
  • [ 1532-72-5 ]
  • [ 24423-87-8 ]
YieldReaction ConditionsOperation in experiment
63% With urea hydrogen peroxide adduct In methanol at 0 - 20℃; for 7 h; General procedure B. To a stirred solution of amine (0.3-0.8 mmol) in methanol (0.5 M) was added at 0 °C UHP (3 mol equiv) and catalyst 1 (2 mol percent). The mixture was stirred at room temperature for the necessary time (see Table 2). The reaction mixture developed a red-orange colour that disappeared at different times depending on the amine type. The reaction mixture, then, remained yellow and in some cases a white precipitate formed. After removal of the solvent under reduced pressure, dichloromethane was added and the slurry formed was filtered through Celite. The solvent was evaporated and the crude residue purified by flash column chromatography.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7079 - 7082
  • 7
  • [ 106824-51-5 ]
  • [ 1532-72-5 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 8, p. 2311 - 2314
  • 8
  • [ 96284-58-1 ]
  • [ 1532-72-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 12, p. 4731 - 4739
  • 9
  • [ 91-21-4 ]
  • [ 119-65-3 ]
  • [ 1532-72-5 ]
Reference: [1] Polish Journal of Chemistry, 2003, vol. 77, # 11, p. 1579 - 1586
  • 10
  • [ 77123-58-1 ]
  • [ 1532-72-5 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 8, p. 2311 - 2314
  • 11
  • [ 6630-33-7 ]
  • [ 1532-72-5 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 8, p. 2311 - 2314
  • 12
  • [ 25705-34-4 ]
  • [ 1532-72-5 ]
Reference: [1] Chemische Berichte, 1936, vol. 69, p. 2766,2768 Anm.6
  • 13
  • [ 1532-72-5 ]
  • [ 1532-84-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 12, p. 4554 - 4557
  • 14
  • [ 1532-72-5 ]
  • [ 1532-71-4 ]
YieldReaction ConditionsOperation in experiment
55% With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
Reference: [1] Organic Letters, 2015, vol. 17, # 12, p. 2948 - 2951
[2] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795
[3] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
[4] Organic Letters, 2016, vol. 18, # 9, p. 1956 - 1959
  • 15
  • [ 1532-72-5 ]
  • [ 115955-90-3 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014
  • 16
  • [ 1532-72-5 ]
  • [ 59139-93-4 ]
Reference: [1] Patent: WO2013/92979, 2013, A1,
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