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[ CAS No. 6267-02-3 ]

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Chemical Structure| 6267-02-3
Chemical Structure| 6267-02-3
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Product Details of [ 6267-02-3 ]

CAS No. :6267-02-3 MDL No. :MFCD00030130
Formula : C15H15N Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :209.29 g/mol Pubchem ID :22647
Synonyms :

Safety of [ 6267-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6267-02-3 ]

  • Upstream synthesis route of [ 6267-02-3 ]
  • Downstream synthetic route of [ 6267-02-3 ]

[ 6267-02-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 73183-55-8 ]
  • [ 6267-02-3 ]
YieldReaction ConditionsOperation in experiment
98% With phosphoric acid In water at 35℃; for 2 h; A mixture of 2-(2-(phenylamino)phenyl)propan-2-ol (3, 1.0 g, 4.5 moles) in 85.0percent> phosphoric acid (15 ml) was stirred at 35 °C for 2h until judged complete by TLC. The reaction mixture was then poured onto crushed ice and the precipitate was filtered, washed with water, and dried to afford the title compound (0.90 g, 98percent> yield) as a white powder. 1H NMR (300 MHz, CDC13) δ 7.39 (d, 2H, J = 8.1 Hz), 7.11 (t, 2H, J = 7.2 Hz), 6.92 (t, 2H, J = 7.2 Hz), 6.71 (d, 2H, J = 7.8 Hz), 6.15 (br s, 1H), 1.61 (s, 6H); LCMS (ESI) m/z 210 (MH+).
98% at 35℃; for 2 h; To a 50 ml one-necked flask was added lg (4.5 mmol) of compound B2, 15 ml (85percent) of phosphoric acid, and stirred at 35 ° C for two hours. The mixture was then poured into 50 ml of ice water to precipitate a solid.After suction filtration, washing with water repeatedly gave 0.98 g of product 83, yield 98percent.
90% at 20℃; for 16 h; 160 mL of an excess amount of phosphoric acid as a solvent was added to Compound 1C(3.26 g, 14.37 mmol), and the mixture was stirred at room temperature. After stirring for 16 hours or longer, 200 to 250 mL of distilled water was slowly added. Thereafter, the mixture was stirred for 0.5 to 1 hour, and a precipitated solid was filtered. An organic layer was extracted from the filtered solid using an aqueous sodium hydroxide solution and a dichloromethane solvent. The extracted organic layer was dehydrated using magnesium sulfate and the remaining organic solvent was removed to obtain a white solid 1D(2.7 g, yield 90percent).
87%
Stage #1: at 20℃; for 12 h;
Preparation of Compound 1-3 [99] After Compound 1-2 (80 g, 0.35 mol) was added to H3PO4 (1.7 L), the mixture was stirred for 12 hours at room temperature. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and the produced solid was filtered while being washed with water. The solid was dissolved with dichloromethane, extracted and neutralized with NaOH. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-3 (64 g, 87percent) was obtained via recrystallization with hexane.
87%
Stage #1: at 20℃; for 12 h;
Stage #3: With sodium hydroxide In dichloromethane
Compound 3-2 (80g, 0.35mol) was added to H3PO4 1.7L and the mixture was stirred at room temperature for 12 hours. After termination of the reaction, the mixture was neutralized with distilled water, and the produced solid was washed with water and filtered. The solid was dissolved in dichloromethane, extracted, and neutralized with NaOH. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently recrystallization was conducted using hexane, yielding Compound 3-3 (64g, 87percent).
87% at 20℃; for 12 h; 80 g (0.35 mole) of the compound obtained in the previous step was added to 1.7L of phosphoric acid and the mixture was stirred for 12 hours at room temperature. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and the produced solid was filtered while being washed with water. The solid was dissolved in dichloromethane, extracted and neutralized with sodium hydroxide. After drying the organic layer with magnesium sulfate and removing the solvent by a rotary type evaporator, 64 g 9,9-dimethyl-9,10-dihydroacridine (87percent) was obtained via recrystallization in hexane.
87% at 35℃; for 2 h; To a flask charged with 2-(2-(phenylamino)phenyl)propan-2-ol (5.00 g, 22.0 mmol) was added phosphoric acid (85percent, 76 mL). The reaction was stirred and heated to 35 °C. After 2 h, the crude reaction mixture was cooled to room temperature and slowly poured onto ice. The mixture was extracted with dichloromethane. The combined organic layers were washed with water and brine. The 10 washed organic layer was dried over Na2S04, filtered and concentrated. The resulting solid product, afforded in 87percent yield, was used without further purification.
69% at 20℃; Inert atmosphere In N2in the gas purification system, the use of a compound "c" (33.1mmol) is added to the excess phosphoric acid solvent (160 ml) in, and the stirring solution at room temperature. The solution and then stirring 16 hours or more, and distilled water is slowly added (200 to 250 ml). Stirring the solution 0.5 to 1 hours, and the precipitated solid filter. The filtering of the solid using aqueous sodium hydroxide solution and dichloromethane solvent extraction. From the extraction of using magnesium sulphate remove the moisture in the organic layer, and removing the organic solvent, so as to obtain a white solid compound "d". (Yield: 69percent)

Reference: [1] Patent: WO2014/165307, 2014, A2, . Location in patent: Paragraph 0316
[2] Patent: CN108191739, 2018, A, . Location in patent: Paragraph 0045; 0046; 0047
[3] Patent: US2018/166636, 2018, A1, . Location in patent: Paragraph 0113; 0114
[4] Patent: WO2011/93609, 2011, A1, . Location in patent: Page/Page column 16
[5] Patent: WO2012/39561, 2012, A1, . Location in patent: Page/Page column 24
[6] Patent: WO2013/45411, 2013, A1, . Location in patent: Paragraph 00101
[7] Patent: KR2018/30860, 2018, A, . Location in patent: Paragraph 0050-0051
[8] Chemische Berichte, 1980, vol. 113, # 1, p. 358 - 384
[9] Patent: CN105585577, 2016, A, . Location in patent: Paragraph 0109; 0110; 0111; 0112
[10] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 2976 - 2993
[11] RSC Advances, 2016, vol. 6, # 25, p. 20588 - 20597
  • 2
  • [ 35708-19-1 ]
  • [ 75-16-1 ]
  • [ 6267-02-3 ]
YieldReaction ConditionsOperation in experiment
81% at 0℃; 20.0 g (88.00 mmol) of the intermediate (A) synthesized in the above step 1 was suspended in terrahydrofuran (293 ml), and then 102.7 ml of methylmagnesium bromide (3M) was slowly added dropwise at 0 ° C. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled under reduced pressure. 100 ml of sulfuric acid diluted to 10percent in distilled water was added to the distillation product, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and recrystallized from dichloromethane and hexane to obtain 15.0 g (yield: 81percent) of the intermediate product (B).
Reference: [1] Patent: KR2016/102142, 2016, A, . Location in patent: Paragraph 0215; 0223; 0224
[2] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081
  • 3
  • [ 38158-59-7 ]
  • [ 6267-02-3 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 5 h; 15 g of 2-isopropyl-N-phenylaniline obtained in Preparation Example 3 was placed in a round bottom three-necked flask,Concentrated sulfuric acid was added dropwise at room temperature and the mixture was stirred.After completion of the dropwise addition,The mixture was further stirred at room temperature for 5 hours. then,The organic layer was washed with ethyl acetate and water, extracted, concentrated and separated by column,9,9-dimethyl-9,10-dihydroacridine (13.4 g, 90percent yield) was obtained.
Reference: [1] Patent: TWI579270, 2017, B, . Location in patent: Paragraph 0097; 0098; 0099
  • 4
  • [ 122-39-4 ]
  • [ 67-64-1 ]
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Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1458,1464
  • 5
  • [ 35708-19-1 ]
  • [ 6267-02-3 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 1, p. 358 - 384
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 2976 - 2993
[3] Patent: WO2011/93609, 2011, A1,
[4] Patent: WO2012/39561, 2012, A1,
[5] Patent: WO2013/45411, 2013, A1,
[6] Patent: WO2014/165307, 2014, A2,
[7] Patent: CN105585577, 2016, A,
[8] Patent: KR2018/30860, 2018, A,
[9] Patent: US2018/166636, 2018, A1,
  • 6
  • [ 91-40-7 ]
  • [ 6267-02-3 ]
Reference: [1] Patent: WO2011/93609, 2011, A1,
[2] Patent: WO2012/39561, 2012, A1,
[3] Patent: WO2013/45411, 2013, A1,
[4] Patent: WO2014/165307, 2014, A2,
[5] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081
[6] Patent: CN105585577, 2016, A,
[7] Patent: KR2018/30860, 2018, A,
[8] Patent: CN108191739, 2018, A,
[9] Patent: US2018/166636, 2018, A1,
  • 7
  • [ 134-20-3 ]
  • [ 6267-02-3 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 1, p. 358 - 384
[2] Patent: KR2016/102142, 2016, A,
  • 8
  • [ 2980-26-9 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1458,1464
  • 9
  • [ 2479-47-2 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1458,1464
  • 10
  • [ 578-95-0 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 11
  • [ 917-64-6 ]
  • [ 611-64-3 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 12
  • [ 578-95-0 ]
  • [ 611-64-3 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 13
  • [ 62-53-3 ]
  • [ 7073-69-0 ]
  • [ 6267-02-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 25, p. 20588 - 20597
  • 14
  • [ 108-86-1 ]
  • [ 6267-02-3 ]
Reference: [1] Patent: KR2016/102142, 2016, A,
  • 15
  • [ 917-64-6 ]
  • [ 142-96-1 ]
  • [ 578-95-0 ]
  • [ 611-64-3 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 16
  • [ 7647-01-0 ]
  • [ 80-05-7 ]
  • [ 122-39-4 ]
  • [ 6267-02-3 ]
  • [ 5650-10-2 ]
Reference: [1] Patent: US2061779, 1932, ,
  • 17
  • [ 7647-01-0 ]
  • [ 7732-18-5 ]
  • [ 62-53-3 ]
  • [ 67-64-1 ]
  • [ 6267-02-3 ]
  • [ 147-47-7 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1458,1464
  • 18
  • [ 6267-02-3 ]
  • [ 1333316-35-0 ]
YieldReaction ConditionsOperation in experiment
90% With bromine In chloroform for 8 h; Inert atmosphere Under a nitrogen atmosphere (N2 purging), Compound 1D(2.7 g, 12.93 mmol) was added to chloroform(200ml), followed by stirring. After stirring, 3 equivalents of bromine were slowly added dropwise. After 8 hours, the reaction was quenched by addition of an aqueous sodium thiosulfate solution. Then, extraction was performed. Thereafter, purification was performed using a column using a developing solvent of methylenechloride(MC):hexane (1:5) to obtain a white solid 1E(4.24 g, yield 90percent).
69% With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; To a stirred solution of 9,9-dimethyl- 10H- acridine (4, 0.50 g, 2.4 mmol) in dry THF (10 mL), was added trimethylphenylammonium tribromide (PTT) (1.8 g, 4.8 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After the reaction was judged complete (TLC), the reaction mixture was poured in water (30 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were dried over anhydrous MgS04, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography with gradient elution (0 to 30percent EtOAc-hexane) to afford the title compound as a light brown oil (0.6 g, 69percent yield). 1H NMR (300 MHz, DMSO- 6) δ 1.47 (s, 6 H) 6.74 (d, J=8.48 Hz, 2 H) 7.22 (dd, J=8.48, 2.26 Hz, 2 H) 7.46 (d, J=2.07 Hz, 2 H) 9.18 (s, 1 H). LCMS (ESI) m/z 368 (MH+).
Reference: [1] Patent: US2018/166636, 2018, A1, . Location in patent: Paragraph 0115; 0116
[2] Patent: WO2014/165307, 2014, A2, . Location in patent: Paragraph 0321
  • 19
  • [ 128-08-5 ]
  • [ 6267-02-3 ]
  • [ 1333316-35-0 ]
Reference: [1] Patent: US2012/319052, 2012, A1,
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