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[ CAS No. 1532-97-4 ]

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Chemical Structure| 1532-97-4
Chemical Structure| 1532-97-4
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CAS No. :1532-97-4 MDL No. :MFCD00006904
Formula : C9H6BrN Boiling Point : 282.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :208.05 g/mol Pubchem ID :73743
Synonyms :

Safety of [ 1532-97-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1532-97-4 ]

  • Upstream synthesis route of [ 1532-97-4 ]
  • Downstream synthetic route of [ 1532-97-4 ]

[ 1532-97-4 ] Synthesis Path-Upstream   1~48

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  • [ 68-12-2 ]
  • [ 22960-16-3 ]
YieldReaction ConditionsOperation in experiment
36%
Stage #1: With n-butyllithium In tetrahydrofuran at -65℃; for 0.5 h; Inert atmosphere
Stage #2: at -65℃; for 1 h; Inert atmosphere
To a solution of 4-bromoisoquinoline 24a (2.0 g, 9.6 mmol) in 30 mL re-distilled THF was added n-butyl lithium (4.0 mL, 10 mmol, 2.5 M in THF) dropwisely at -65° C. under N2 atmosphere.
The resulting mixture was stirred for 30 mm at this temperature before N,N-dimethylformamide (730 mg, 10 mmol) was added dropwise, and stirred for additional 1 h at this temperature.
After the reaction was over, 100 mL saturated aq. NH4Cl was added to the reaction mixture, and the mixture was extracted with EtOAc (50 mL*3).
The combined organic layers were washed with 100 mL brine, dried over anhydrous Na2SO4, concentrated under reduced pressure.
The crude was purified by silica gel column chromatography (0-100percent EtOAc/PE) to give isoquinoline-4-carbaldehyde 31a (550 mg, yellow solid, yield: 36percent).
1H NMR (400 MHz, CDCl3): δ 10.41 (s, 1H), 9.45 (s, 1H), 9.22 (d, J=8.4 Hz, 1H), 8.96 (s, 1H), 8.10 (d, J=8.4 Hz, 1H), 7.96-7.92 (m, 1H), 7.76 (t, J=8.4 Hz, 1H).
Reference: [1] Tetrahedron, 1998, vol. 54, # 35, p. 10317 - 10328
[2] European Journal of Organic Chemistry, 2009, # 26, p. 4458 - 4467
[3] Patent: US2017/37050, 2017, A1, . Location in patent: Paragraph 0346-0349
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  • [ 22960-16-3 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 45, p. 7889 - 7892
  • 3
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  • [ 50978-45-5 ]
  • [ 22960-16-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8611 - 8615[2] Angew. Chem., 2013, vol. 125, # 33, p. 8773 - 8777,5
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  • [ 109-72-8 ]
  • [ 22960-16-3 ]
Reference: [1] Patent: US4584379, 1986, A,
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  • [ 82102-37-2 ]
  • [ 5470-80-4 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 6112 - 6120
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  • [ 23687-25-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 1, p. 137 - 149
[2] Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10028 - 10029
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[4] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
[5] Organic Letters, 2014, vol. 16, # 2, p. 556 - 559
[6] Journal of the American Chemical Society, 1942, vol. 64, p. 783
[7] Patent: US2005/20623, 2005, A1, . Location in patent: Page 104
[8] Patent: WO2013/13816, 2013, A1,
[9] Patent: US2013/29995, 2013, A1,
[10] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 4, p. 803 - 806
  • 7
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium amide In 1,2-dimethoxyethane at 80℃; for 20 h; Sealed vial
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333 h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water
4-Bromo-/5O-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdCl2 (7.30 mg, 1.00 x 10"2 mmol), and LiNH2 (0.230 g, 10.0 mmol) in 20.0 mL DME gave 0.118 g (82percent) of 4-Amino-/.yoe-quinoline as a solid.
80%
Stage #1: With ammonia; sodium t-butanolate In 1,2-dimethoxyethane at 90℃; for 20 h;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333 h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water
4-Bromo-λyoe-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdCl2 (7.30 mg, 1.00 x 10"2 mmol), and NaOtBu (0.192 g, 2.00 mmol) in 20.0 mL DME gave 0.115 g (80percent) of 4-amino-/-"?-quinoline as a solid Ethyl acetate/methanol: 50/50). 1H NMR (CDCl3) δ 8.70 (s, 1 H), 8.00 (s, 1 H), 7.84 (d, J= 8.0 Hz, 1 H), 7.76 (d,. J = 8.5 Hz, 1 H), 7.58 (dd, J = 8.0, 7.0 Hz, 1 H), 7.51 (dd, J= 8.0, 7.5 Hz, 1 H), 4.21 (s, 2 H); 13C NMR (CDCl3) δ 142.99, 136.86, 128.86, 128.54, 127.99, 127.65, 126.93, 125.95, 119.97.
Reference: [1] Patent: WO2007/109365, 2007, A2, . Location in patent: Page/Page column 48-49; 52
[2] Patent: WO2007/109365, 2007, A2, . Location in patent: Page/Page column 44; 45; 47
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  • [ 194032-33-2 ]
Reference: [1] Patent: EP1074545, 2001, A1,
  • 9
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  • [ 394-67-2 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With n-butyllithium In tetrahydrofuran at -65℃; for 0.5 h;
Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -65℃; for 2 h;
To a solution of n-butyl lithium (133 mL, 332.5 mmol, 2.5 M in THF) in 760 mL THF was added a solution of 4-bromoisoquinoline 24a (20 g, 96.6 mmol) in 144 mL THF dropwise at -65° C. and the resulting mixture was stirred at this temperature for another 30 mm after the completion of addition.
A solution of N-fluorobenzenesulfonimide (66.68 g, 211.7 mmol) in 216 mL THF was added at -65° C. in 1 h dropwisely.
After being stirred for another 1 h at this temperature, the reaction mixture was warmed to room temperature slowly with stirring, after the reaction is over, 300 mL saturated aq. NH4Cl was added slowly, extracted with EtOAc (300 mL*3).
The combined organic layers were washed with 300 mL brine, dried over anhydrous Na2SO4 and concentrated.
The crude product was purified by silica gel column chromatography (0-100percent EtOAc/PE) to give 4-fluoroisoquinoline 24b (8.5 g, red oil, yield: 60percent).
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3792 - 3795
[2] Patent: US2017/37050, 2017, A1, . Location in patent: Paragraph 0301; 0302
[3] Patent: US2007/179127, 2007, A1, . Location in patent: Page/Page column 47-48
[4] Patent: US2009/48223, 2009, A1, . Location in patent: Page/Page column 101
[5] Patent: US2010/93789, 2010, A1, . Location in patent: Page/Page column 46
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YieldReaction ConditionsOperation in experiment
23.8% at 100℃; lntermediate-12: 3-Bromoisoquinoline: To a stirred solution of isoquinoline (24 g, 186 mmol) in AcOH (50 mL) was added NBS (36.2 g, 204.6 mmol) at RT and the reaction mixture was heated to 100 2C overnight. Then it was cooled to RT and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (5percent EtOAc:Hexanes) to furnish the title compound (9.2 g, 23.8percent) as an oil.
Reference: [1] Patent: WO2013/5168, 2013, A2, . Location in patent: Page/Page column 40
[2] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 199
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 3030
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 3030
[5] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
[6] Journal of the American Chemical Society, 1945, vol. 67, p. 1268
[7] Synthesis, 2002, # 1, p. 83 - 86
[8] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263
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Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 5, p. 845 - 848
  • 12
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
  • 13
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Chemical & Pharmaceutical Bulletin, 1988, vol. 36, # 3, p. 930 - 939
  • 16
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 199
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
  • 23
  • [ 118798-87-1 ]
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  • [ 107-13-1 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2258 - 2262
  • 24
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424
  • 25
  • [ 87777-05-7 ]
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  • [ 87-72-9 ]
Reference: [1] Carbohydrate Research, 1993, vol. 250, # 1, p. 79 - 86
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  • [ 2280-44-6 ]
Reference: [1] Carbohydrate Research, 1993, vol. 250, # 1, p. 79 - 86
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Reference: [1] Yakugaku Zasshi, 1931, vol. 51, p. 73[2] Chem. Zentralbl., 1931, vol. 102, # II, p. 2330
[3] Yakugaku Zasshi, 1928, vol. 48, # 9, p. 109[4] Chem. Zentralbl., 1931, vol. 102, # II, p. 2330
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YieldReaction ConditionsOperation in experiment
27.4% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 120℃; Inert atmosphere lntermediate-13: lsoquinolin-4-carbonitrile: To a stirred solution of 3-bromoisoquinoline (lntermediate-12) (9.2 g, 44.2 mmol) in DMF (15 mL) were added, Pd(PPh3)4 (10.2 g, 8.84 mmol) and Zn(CN)2 (10.34 g, 88.44 mmol, 2.0 eq) and the solution was degassed with N2 for 20 min. It was then heated to 120 2C overnight. After the completion (TLC), reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (10percent EtOAc:Hexanes) to afford the desired compound (3.4 g, 27.4percent) as pale yellow solid.
Reference: [1] Patent: WO2013/5168, 2013, A2, . Location in patent: Page/Page column 40
  • 29
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  • [ 544-92-3 ]
  • [ 34846-65-6 ]
YieldReaction ConditionsOperation in experiment
58% at 150 - 230℃; Example 64: Synthesis of 4-(3-(2-fluoro-4-methoxybenzylidene)-3 ,4,5,6- 5 tetrahydropyridin-2-yl)isoquinoline dihydrochloride.; The preparation of 4-(3-(2-fluoro-4-methoxybenzylidene)-3,4,5,6- tetrahydropyridin-2-yl)isoquinoline dihydrochloride is described below.; A. Step 1: Preparation of Intermediate 9; Intermediate 9 was prepared as described in Tyson, F.T. J. Am. Chem. Soc, 1939, 61 (I )5 183 -185. Briefly, 4-Bromoisoquinoline (3.36 g, 16.2 mmol) and Cu(I)CN (2.17 g, 24.2 mmol) were combined as the dry solids in a round bottom flask fitted with a magnetic stirrer and vigeraux column under N2. Heat was applied.15 At approximately 1500C, the mixture began to stir freely. At approximately 23O0C, the reaction mixture formed a black solid that began to splatter onto the sides of the flask. The reaction was cooled to room temperature and treated with concentrated NH4OH overnight. This mixture was then extracted 3 times with EtOAc. The EtOAc extracts were washed with dilute NH4OH(Hq) and brine, then combined, dried 0 over Na2SO4, treated with decolorizing charcoal, filtered through celite, then concentrated under reduced pressure. The recovered material was dissolved into a mixture of hot isopropanol and methanol to re-crystallize. The crystals were recovered by vacuum filtration, washed with fresh isopropanol and dried under vacuum giving 1.47 g (58percent) of yellow crystals. LC-MS: RT = 7.86 min, [M+H]+ = 5 155.1.
Reference: [1] Synthetic Communications, 2004, vol. 34, # 1, p. 137 - 149
[2] Patent: WO2007/89626, 2007, A2, . Location in patent: Page/Page column 71
[3] Archiv der Pharmazie, 1993, vol. 326, # 10, p. 785 - 790
[4] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263
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YieldReaction ConditionsOperation in experiment
44.6% at 250℃; for 0.75 h; To 4-bromo isoquinoline (2 g, 9.613 mmol) is added copper (I) cyanide (1.29 g, 14.42 mmol), and the mixture is heated to 250° C. for 45 minutes, where the pressure is taken down to 5-10 torr.
The mixture which turns black at this point begins to distil over, giving crystals in the condenser.
The condenser is cleaned with dichloromethane and the volatiles in the solution are removed in vacuo to give the desired product (0.66 g, 44.6percent) as colorless crystals.
Reference: [1] Patent: US2006/276515, 2006, A1, . Location in patent: Page/Page column 44
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Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3303 - 3305
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1540 - 1545
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Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 21, p. 6249 - 6254
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Reference: [1] Synlett, 2007, # 4, p. 555 - 558
[2] Synthesis, 2008, # 20, p. 3351 - 3355
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Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 860 - 863
  • 36
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  • [ 66728-98-1 ]
Reference: [1] Pharmaceutical Bulletin, 1954, vol. 2, p. 72,76
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 2, p. 939 - 950
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
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YieldReaction ConditionsOperation in experiment
94% With 3-chloro-benzenecarboperoxoic acid In chloroform 13A.
4-Bromoisoquinoline 2-oxide
A solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) in chloroform (100 mL) was added dropwise over 1 h to a solution of 70percent mCPBA (12.4 g, 50.3 mmol) in chloroform (100 mL) at rt.
After stirring 18 h, the reaction mixture was washed with 1 N NaOH (2*150 mL), dried (MgSO4) and concentrated under reduced pressure to afford compound 13A (4.23 g, 94percent) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H, J=8 Hz), 7.70 (m, 3H).
94% With 3-chloro-benzenecarboperoxoic acid In chloroform 13A.
4-Bromoisoquinoline 2-oxide
A solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) in chloroform (100 mL) was added dropwise over 1 h to a solution of 70percent mCPBA (12.4 g, 50.3 mmol) in chloroform (100 mL) at rt.
After stirring 18 h, the reaction mixture was washed with 1 N NaOH (2*150 mL), dried (MgSO4) and concentrated under reduced pressure to afford compound 13A (4.23 g, 94percent) as an off-white solid. 1H NMR(400 MHz, CDCl3) .box. 8.71 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H, J=8 Hz), 7.70 (m, 3H).
57.6% With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 3 h; 2d) 4-BROMO-1-CHLORO-ISOQUINOLINE To a solution of 4-bromoisoquinoline (52. 08 g, 0. 250 MOL) in methylene chloride (600 mL) is added m-chloroperbenzoic acid (64.47 g, 0.250 MOL). The mixture is stirred for 2.5 hours. To the mixture is added 1.5 g of m-chloroperbenzoic acid and the mixture is stirred for 30 minutes. The solution is washed with 1 N NAOH, brine, and then dried over sodium sulfate. The solvent is removed to give a white solid. The solid is crystallized from hot acetone to yield 32.22 g (57.6percent) of a white SOLID. 1H, 13C NMR consistent with structure. The N-oxide (15.75 g, 0.0703 mol) is dissolved in chloroform (50 mL) and cooled in an ice bath. Phosphorus OXYCHLORIDE (20 mL) is added dropwise and then the mixure is warmed to room temperature and then heated to reflux for 1.5 hours. The mixture is allowed to cool to room temperature and is then poured over ice. The aqueous mixture is neutralized to pH 7-8 with NAHCO3 AND then extracted with chloroform. The organic phase is washed with brine, dried over sodium sulfate and the solvent is removed. The residue is purified by flash chromatography (SIO2/5percent ETHYL acetate/hexanes). Collected 12.22 g (72percent). M+H = 389. 'H NMR ; 5 8. 50 (s, 1H), 8.40 (d, 1H), 8.20 (d, 1H), 7.92 (t, 1H), 7.79 (t, 1H).
94% With 3-chloro-benzenecarboperoxoic acid In chloroform A.
4-Bromo-isoquinoline 2-oxide (470A)
A solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) in 100 mL of chloroform was added dropwise over 1 h to a solution of 70percent mCPBA (12.4 g, 50.3 mmol) in 100 mL of chloroform at room temperature.
After stirring 18 h, the reaction mixture was washed with 1N NaOH (2*150 mL), dried over magnesium sulfate and concentrated in vacuo to afford 4.23 g (94percent) of compound 470A as an off-white solid. 1H NMR-400 MHz (CDCl3): δ 8.71 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H, J=8 Hz), 7.70 (m, 3H).

Reference: [1] Patent: US2004/19063, 2004, A1,
[2] Patent: US2004/181064, 2004, A1,
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4234 - 4243
[4] Chemical Communications, 2018, vol. 54, # 32, p. 3977 - 3980
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825
[6] Organic Process Research and Development, 2006, vol. 10, # 1, p. 70 - 77
[7] Patent: WO2005/28444, 2005, A1, . Location in patent: Page/Page column 51
[8] Pharmaceutical Bulletin, 1954, vol. 2, p. 72,76
[9] Patent: US2004/77605, 2004, A1,
[10] Patent: US2005/119228, 2005, A1,
[11] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 2, p. 939 - 950
[12] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[13] New Journal of Chemistry, 2016, vol. 40, # 12, p. 10227 - 10232
[14] Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3165 - 3169
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Reference: [1] Patent: US2002/103203, 2002, A1,
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  • [ 33930-63-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5081 - 5085
[2] Green Chemistry, 2018, vol. 20, # 14, p. 3302 - 3307
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YieldReaction ConditionsOperation in experiment
89% at 0 - 20℃; for 1 h; 4-Bromo-5-nitroisoquinoline (11). Potassium nitrate (5.34 g; 0.052 mol) was added to 20 mL of concentrated sulfuric acid and slowly dissolved by careful heating. The resulting solution was added dropwise to a solution of 4-bromoisoquinoline (10 g, 0.048 mol) dissolved in 40 mL of the same acid at O0C. After removal of the cooling bath, the solution was stirred for one hour at room temperature. The reaction mixture was then poured onto crushed ice (400 g) and made basic with ammonium hydroxide. The resulting yellow precipitate was collected by filtration and the filtrate was extracted with diethyl ether (3 x 500 mL), dried (Na2SO4), and concentrated to give a yellow solid that was combined with the initial precipitate. Recrystallization from methanol gave 12.1 g (89percent) of 11 as slightly yellow crystals
89% With potassium nitrate In sulfuric acid at 0 - 20℃; for 1 h; Potassium nitrate (5.34 g; 0.052 mol) was added to 20 mL of concentrated sulfuric acid and slowly dissolved by careful heating.
The resulting solution was added dropwise to a solution of 4-bromoisoquinoline (10 g, 0.048 mol) dissolved in 40 mL of the same acid at 0° C.
After removal of the cooling bath, the solution was stirred for one hour at room temperature.
The reaction mixture was then poured onto crushed ice (400 g) and made basic with ammonium hydroxide.
The resulting yellow precipitate was collected by filtration and the filtrate was extracted with diethyl ether (3*500 μL), dried (Na2SO4), and concentrated to give a yellow solid that was combined with the initial precipitate.
Recrystallization from methanol gave 12.1 g (89percent) of 11 as slightly yellow crystals: mp 172-174° C.; 1H NMR (300 MHz, CDCl3) δ 9.27 (s, 1H); 8.87 (s, 1H); 8.21 (dd, 1H, J=6.6, 1.2 Hz); 7.96 (dd, 1H, J=6.6, 1.2 Hz); 7.73 (t, 1H, J=7.5 Hz); CIMS m/z 253 (M+H+, 100percent); 255 (M+H++2, 100percent); Anal. Calc'd for C9H5BrN2O2: C, 42.72; H, 1.99; N, 11.07. Found: C, 42.59; H, 1.76; N, 10.87.
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 6, p. 1403 - 1412
[2] Patent: WO2006/12640, 2006, A2, . Location in patent: Page/Page column 43
[3] Patent: US2007/155720, 2007, A1, . Location in patent: Page/Page column 20
[4] Patent: US2002/132827, 2002, A1,
[5] Patent: US6413977, 2002, B1,
[6] Patent: US2005/20623, 2005, A1, . Location in patent: Page 115
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