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[ CAS No. 15679-03-5 ]

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2D
Chemical Structure| 15679-03-5
Chemical Structure| 15679-03-5
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CAS No. :15679-03-5MDL No. :MFCD01628084
Formula : C13H8ClN Boiling Point : 377.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :213.66Pubchem ID :269968
Synonyms :

Computed Properties of [ 15679-03-5 ]

TPSA : 12.9 H-Bond Acceptor Count : 1
XLogP3 : 4.4 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 15679-03-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15679-03-5 ]

  • Upstream synthesis route of [ 15679-03-5 ]
  • Downstream synthetic route of [ 15679-03-5 ]

[ 15679-03-5 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
96% for 3 h; Reflux Phosphorus oxychloride (15 ml) and dimethylaniline (0.63 ml) were added to phenanthridine (2.0 g), followed by refluxing for 3 hours. The solution was poured into H2O to generate a solid, and the obtained solid was extracted with chloroform, followed by drying with sodium sulfate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The obtained solid was purified by column chromatography (eluent: chloroform) (amount: 2.1 g, yield: 96percent).1H HNR (300 MHz, CDCl3, TMS, RT): δ 8.63-8.60 (1H, d), 8.55-8.52 (1H, d), 8.50-8.48 (1H, d), 8.11-8.09 (1H, d), 7.94-7.92 (1H, t), 7.79-7.66 (3H, m)
96% for 1 h; Reflux Step 1
Phenanthridinone (5.0 grams, 0.027 mole) was added to a reaction flask containing phosphorus pentachloride (6.1 grams, 0.29 mole) and 50 mL of phosphoryl chloride. The reaction mixture was refluxed for 1 hour, cooled to room temperature and diluted with toluene. The excess phosphoryl chloride and toluene were removed on a rotary evaporator. The residue was dissolved into ethyl acetate and washed with distilled water followed by brine. The solvent layer was dried over magnesium sulfate, filtered and concentrated to give pl2-i1 (5.5 grams, 96percent) as an off-white solid. The product was confirmed by Mass Spectrometry and 1H NMR and used directly in the next step.
96% With phosphorus pentachloride; trichlorophosphate In toluene for 1 h; Reflux Step 1 phenanthridinone (5.0 g, 0.027 mol) phosphorus pentachloride was added to the reaction flask containing 50ml phosphoryl chloride (6.1 g, 0.29 mole) . The reaction mixture was refluxed for one hour, cooled to room temperature and diluted with toluene. The excess phosphoryl chloride and toluene were removed on a rotary evaporator. The residue was dissolved in ethyl acetate and then in distilled water and washed with brine. To give a solvent layer was dried over magnesium sulfate, filtered and concentrated i1-pl2 (5.5 g, 96percent) as an off-white solid by. The product was confirmed by mass spectra and 1H NMR, which was used directly in the next step.
88.1% at 100℃; for 2 h; Inert atmosphere The present embodiment provides 6-chlorphenanthridine (structural formula :) synthesis route, as shown in Figure 1, specificallyThe 6 (5H) -phenanthridinone (5.11 g, 26.2 mmol) and phosphorus pentachloride (6.12 g, 29.4 mmol) were placed in a 250 ml single portFlask,Add 50ml phosphorus oxychloride,The mixture was refluxed for 2 hours at 100 ° C under nitrogen protection; cooled to room temperature,Add 50ml toluene diluted reaction solution,Then the excess phosphorus oxychloride spin to most,Residual liquid slowly poured into 2mol / L of ammonia,The precipitated solid was extracted three times with 100 ml of ethyl acetate; washed with water,Dried over anhydrous magnesium sulfate and dried to give 5.1 g of light yellow product.The crude product was purified by silica gel column chromatography (EA: PE = 2: 3, v / v, the same below)4.93 g of yellow flake solid were isolated with a yield of 88.1percentAs shown in Figure 1.
87% at 100℃; for 24 h; Inert atmosphere Phenanthridin-6(5H)-one (1; 0.100 g, 0.492 mmol) was placed in aSchlenk flask under argon. POCl3 (3.29 g, 2 mL, 21.4 mmol, 43 equiv)was added, and the mixture was stirred at 100 °C for 24 h. The mixturewas cooled, poured onto ice, and stirred for 15 min. The solidthat formed was collected by filtration, washed thoroughly with H2O,and dried in vacuum to give a light-brown solid; yield: 95.5 mg (87percent);Rf = 0.65 (hexane–EtOAc, 5:1; detection: UV).IR (KBr): 3103, 3072, 3039, 1613, 1574, 757 cm–1.1H NMR (600 MHz, acetone-d6): δ = 7.69 (ddd, J = 8.2, 7.0, 1.4 Hz, 1 H,H-12), 7.75 (ddd, J = 8.2, 7.0, 1.5 Hz, 1 H, H-13), 7.77 (ddd, J = 8.2, 7.0,1.2 Hz, 1 H, H-4), 7.91 (ddd, J = 8.3, 7.0, 1.3 Hz, 1 H, H-5), 8.10 (ddd,J = 8.2, 1.4, 0.6 Hz, 1 H, H-14), 8.48 (ddd, J = 8.2, 1.3, 0.6 Hz, 1 H, H-3),8.54 (ddt, J = 8.3, 1.5, 0.6 Hz, 1 H, H-11), 8.62 (ddt, J = 8.3, 1.2, 0.3 Hz, 1H, H-6).13C NMR (151 MHz, acetone-d6): δ = 151.45 (C-2), 143.31 (C-8),134.51 (C-10), 131.77 (C-5), 129.36 (C-13), 129.32 (C-14), 128.25 (C-4), 127.74 (C-3), 127.49 (C-12), 124.90 (C-9), 124.03 (C-7), 122.28 (C-6), 122.21 (C-11). MS (ESI): m/z (percent) = 214.1 [M + H]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C13H9ClN: 214.0148; found:214.0149.
53%
Stage #1: With trichlorophosphate In 2,3-Dimethylaniline for 3 h; Reflux
Stage #2: With ammonium hydroxide In water at 20℃;
synthesis of the compound of the following Formulas 2-F [Show Image] 6-(5H)-phenanthridinone (19.5 g 100 mmol) was added to the dispersion solution of phosphorus oxychloride (POCl3) (150 ml) and dimethylaniline (6 mL). The mixture was continuously agitated, refluxed for about 3 hours, and cooled to room temperature. Phosphorus oxychloride was distilled under the reduced pressure and removed, the remaining material was added to iced water, it was neutralized with the NH4OH solution and extracted with chloroform (3 x 200 mL). The collected chloroform organic layer was washed with 200 mL water, dried with anhydrous magnesium sulfate, and distilled under the reduced pressure. Under the Hexane : CH2Cl2 = 20 : 1 condition, through the column chromatography, the compound of Formula 2-F (11.3 g, 53percent) was manufactured. MS: [M+H]+= 214

Reference: [1] Patent: US2011/201802, 2011, A1, . Location in patent: Page/Page column 10
[2] Patent: US9281483, 2016, B2, . Location in patent: Page/Page column 83
[3] Patent: KR2016/30582, 2016, A, . Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166
[4] Dalton Transactions, 2014, vol. 43, # 44, p. 16872 - 16879
[5] Patent: CN105949246, 2016, A, . Location in patent: Paragraph 0025; 0044-0046; 0049
[6] Synthesis (Germany), 2015, vol. 47, # 22, p. 3479 - 3488
[7] Patent: EP2327679, 2011, A2, . Location in patent: Page/Page column 31-32
[8] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 248
[9] Journal of the Chemical Society, 1956, p. 1498,1506
[10] Journal of the Chemical Society, 1951, p. 3211,3215
[11] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9693 - 9707
[12] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6805 - 6810
[13] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 333 - 339
[14] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 415 - 426
[15] Patent: JP2015/101570, 2015, A, . Location in patent: Paragraph 0030
  • 2
  • [ 5346-21-4 ]
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YieldReaction ConditionsOperation in experiment
91% With thionyl chloride; sulfuryl dichloride; titanium tetrachloride In toluene at -10 - 0℃; Reflux Reaction flask was added Intermediate I (41.6g, 0.21mol) and 100mL of toluene, and stirred and dissolved; In another reaction flask, the sulfonyl chloride (43g, 0.32mol), thionyl chloride (74g, 0.63mol )And titanium tetrachloride (80g, 0.42mol) were mixed and cooled to -10 ~ 0 , and then a toluene solution of Intermediate I was slowly added to the system, the system was maintained during the addition at -10 ~ 0 ;After joining,The system is heated to reflux and the reaction 18-24h, sulfur dioxide and hydrogen chloride escapes, the reaction was monitored by HPLC process; when HPLC showed that the system of Intermediate I content of less than 1percent, heating was stopped,The reaction mixture was added dropwise to a mixture of aqueous ammonia and water at -10 to 0 ° C, and the mixture was stirred at room temperature for 2 hours. Control the rate of drop to ensure that the system termination temperature of -10 ~ 0 . The organic phase was concentrated and recrystallized from n-heptane to give 40.7 g of 6-chlorophenanthrene in a yield of 91percent and a purity of 99.5percent. The filtrate was concentrated under reduced pressure, and the filtrate was concentrated to dryness.
Reference: [1] Patent: CN105906565, 2016, A, . Location in patent: Paragraph 0051; 0052; 0053
[2] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
  • 3
  • [ 79-37-8 ]
  • [ 1015-89-0 ]
  • [ 15679-03-5 ]
YieldReaction ConditionsOperation in experiment
42% at 0 - 20℃; Inert atmosphere; Reflux A stream of nitrogen into the reaction flask, 500mL of dimethylformamide 50mL was stirred at 0 conditions, oxazolyl ildi claw LaAnd dropping the upgrade 61mL (64mmol) slowly. While stirring slowly raising the temperature to room temperature, and the compound [241-3]By heating after adding 50g (26mmol) and stir gently reflux. After the reaction and extracted with dichloromethane, and saturated brine. UAnd by separating the base layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Concentrate the column chromatography methodThe use, to obtain the intermediate compound [241-5] 23g (42percent) was prepared.
Reference: [1] Patent: KR2015/88163, 2015, A, . Location in patent: Paragraph 0290; 0295-0297
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Reference: [1] Patent: EP446604, 1991, A2,
  • 5
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767
  • 6
  • [ 15999-44-7 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
  • 7
  • [ 486-25-9 ]
  • [ 15679-03-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6805 - 6810
[2] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 333 - 339
[3] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 415 - 426
  • 8
  • [ 2157-52-0 ]
  • [ 15679-03-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6805 - 6810
[2] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 333 - 339
[3] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 415 - 426
  • 9
  • [ 87861-97-0 ]
  • [ 15679-03-5 ]
Reference: [1] Yakugaku Zasshi, 1943, vol. 63, p. 177,181[2] Chem.Abstr., 1951, p. 628
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
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Reference: [1] Journal of the Chemical Society, 1950, p. 703,705
[2] Yakugaku Zasshi, 1947, vol. 67, p. 74[3] Chem.Abstr., 1951, p. 9544
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Reference: [1] Yakugaku Zasshi, 1947, vol. 67, p. 74[2] Chem.Abstr., 1951, p. 9544
[3] Journal of the Chemical Society, 1950, p. 703,705
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  • [ 6747-35-9 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 248
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  • [ 173379-08-3 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
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  • [ 17613-40-0 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 22, p. 2295 - 2296
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