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Product Details of [ 71825-51-9 ]

CAS No. :71825-51-9 MDL No. :MFCD00844930
Formula : C10H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XZVURMRLCAFELZ-UHFFFAOYSA-N
M.W : 190.20 Pubchem ID :823615
Synonyms :

Calculated chemistry of [ 71825-51-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.28
TPSA : 69.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 0.35
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.454 mg/ml ; 0.00239 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.0854 mg/ml ; 0.000449 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.388 mg/ml ; 0.00204 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 71825-51-9 ]

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

Application In Synthesis of [ 71825-51-9 ]

* 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.

  • Upstream synthesis route of [ 71825-51-9 ]
  • Downstream synthetic route of [ 71825-51-9 ]

[ 71825-51-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 71825-51-9 ]
  • [ 115279-57-7 ]
YieldReaction ConditionsOperation in experiment
95% With tin(ll) chloride In ethyl acetate for 2.5 h; Reflux which is subsequently reduced to the amine 2-3.
95% With tin(ll) chloride In ethyl acetate for 2.5 h; Reflux 10556] The above reaction scheme illustrates the synthesis of a compound of the invention 2-13. Methylation of starting material 2-1 yields compound 2-2, which is subsequently reduced to the amine 2-3. In a separate reaction, compound 2-4 is converted to a salt, such as an HC1 salt, which is then reacted, for example, with 2-nitrovinyl-hydroxylamine to yield compound 2-6. Further cyclization yields compound 2-7. Halogenation with a reagent such as POd3 results in compound 2-8, which can be coupled with intermediate 2-3 to yield 2-9. The nitro moiety of 2-9 is subsequently reduced to an amine, and a further reaction with 4-nitrophenyl carbonochloridate results in the heterocycle 2-11. The desired compound 2-13 is then prepared by coupling to the benzoxazolyl boronate 2-12, for example in a Suzuki coupling.
95% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; To a suspension of 4-nitrophenylacetonitrile 1 (1.0 equiv, 4.50 g, 27.8 mmol), tetrabutyl ammonium bromide (TBAB, 0.448 g, 1.39 mmol, 0.05 equiv) and iodomethane (11.8 g, 83.4 mmol, 3.0 equiv) in dichloromethane (DCM, 40.0 mL) was added sodium hydroxide (2.78 g, 69.5 mmol, 2.5 equiv) in water (40.0 mL) dropwise.
After stirring at room temperature for 8 h, the organic layer was separated, washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuo.
Then the residue was subjected to flash column chromatography using EA/PE (1:14-1:7) as eluent to furnish the di-methylated product as a white crystal. Yield: 83percent; ESI-MS: m/z = 191 [M+H]+.
The di-methylated product (4.38 g, 23.1 mmol) and 10percent Pd/C (10percent of the substrate, w/w) were shacked in methanol (60.0 mL) and the mixture was stirred at room temperature under H2 (balloon) atmosphere overnight.
After this time, Pd/C was filtered and the filtrate was concentrated in vacuo to provide 2 as a colorless oil, which slowly solidified and was used for the next step without purification. Yield: 95percent. ESI-MS: m/z = 161 [M+H]+.
93% With iron; ammonium chloride In ethanol at 120℃; for 6 h; A solution of 9.4 g (0.35 mol) of iron powder, 37.2 g (0.694 mol) of ammonium chloride solution (37.2 g of ammonium chloride / 40 ml of water) was added successively to 22 g (0.115 mol) of intermediate 4 dissolved in 300 ml of absolute ethanol, 120 ° C reflux reaction 6h,The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was dried by filtration. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 : LO, V: V), was light yellow oily liquid intermediates 5 17.23g, yield 93 ,
89% With tin(ll) chloride In ethyl acetate at 20℃; 2-methyl-2-(4-nitro-phenyl)-propionitrile was dissolved in ethyl acetate (20ml) and treated with stannous chloride dihydrate (3.52g, 15.86mmol). After stirring overnight at room temperature, the reaction mixture was basified with aqueous sodium carbonate. The organic layer was separated, washed with water, dried and concentrated to oil. The crude compound was purified by column chromatography over silica gel using ethyl acetate/pet ether (1:9) as eluent to give 2-(4-aminophenyl)-2-methyl propionitrile (0.45g, 89percent) as oil.
80% With hydrogen In methanol at 20℃; for 2.5 h; 10percent Pd/C (300 mg) was added to a solution of 2-methyl-2-(4-nitro-phenyl)- propionitrile (3.00 g; 15.8 mmol), prepared as in l(A), in MeOH (65 mL). The mixture was hydrogenated at 1 bar at room temperature for 2.5 hours, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (2.40 g; 80percent yield).LCMS (RT): 0.78 min (Method A); MS (ES+) gave m/z: 161.1 (MH+).
74% With hydrogen In tetrahydrofuran; methanol at 20℃; for 10 h; 2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney- Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.Yield: 10 g (74 percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.091-7.119 (d, 2H, J= 8.4Hz), 6.533- 6.561 (d, 2H, J= 8.4Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).
74% With hydrogen In tetrahydrofuran; methanol at 20℃; for 10 h; Step 2:
2-(4-Aminophenyl)-2-methylpropanenitrile
2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney-Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness.
The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.
Yield: 10 g (74percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.091-7.119 (d, 2H, J=8.4 Hz), 6.533-6.561 (d, 2H, J=8.4 Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).
3.5 g With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 15 h; 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g, 23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mL ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).
3.5 g With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 15 h; 10208] 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g,23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mE ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4834 - 4848
[2] Patent: US2009/137595, 2009, A1,
[3] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 119
[4] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0555; 0556
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596
[6] Patent: CN104411706, 2016, B, . Location in patent: Paragraph 0201-0202
[7] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 50
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 17, p. 2203 - 2214
[9] Patent: WO2008/117175, 2008, A2, . Location in patent: Page/Page column 98
[10] Patent: WO2011/1212, 2011, A1, . Location in patent: Page/Page column 38
[11] Patent: US2012/108627, 2012, A1, . Location in patent: Page/Page column 16
[12] Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 1203,1207[13] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 210,214
[14] Journal of Medicinal Chemistry, 1979, vol. 22, # 12, p. 1460 - 1464
[15] Patent: WO2006/65646, 2006, A1, . Location in patent: Page/Page column 21-22
[16] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1027 - 1030
[17] Patent: WO2005/54238, 2005, A1, . Location in patent: Page/Page column 99
[18] Patent: WO2008/64093, 2008, A2, . Location in patent: Page/Page column 18
[19] Patent: WO2013/23119, 2013, A1, . Location in patent: Page/Page column 28
[20] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[21] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 74
[22] Patent: EP2896622, 2015, A1, . Location in patent: Paragraph 0135; 0136
[23] Patent: US2015/239885, 2015, A1, . Location in patent: Paragraph 0207; 0208
[24] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 359
[25] Patent: CN103254203, 2016, B, . Location in patent: Paragraph 0065; 0087; 0088
[26] Patent: US9358229, 2016, B2, . Location in patent: Page/Page column 19; 20
[27] Patent: WO2006/122806, 2006, A2, . Location in patent: Page/Page column 49
  • 2
  • [ 71825-51-9 ]
  • [ 115279-57-7 ]
Reference: [1] Patent: US2012/108583, 2012, A1, . Location in patent: Page/Page column 29
  • 3
  • [ 555-21-5 ]
  • [ 74-88-4 ]
  • [ 71825-51-9 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium t-butanolate In N,N-dimethyl-formamide at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃;
A suspension of sodium tert-butoxide (662 mg, 6.47 mmol) in DMF (20 mL) at 0° C. was treated with 4-nitrophenylacetonitrile (1000 mg, 6.18 mmol) and stirred for 10 min.
Methyl iodide (400 μL, 6.47 mmol) was added dropwise over 15 min.
The solution was stirred at 0-10° C. for 15 min and then at room temperature for additional 15 min.
To this purple solution was added sodium tert-butoxide (662 mg, 6.47 mmol) and the solution was stirred for 15 min.
Methyl iodide (400 μL, 6.47 mmol) was added dropwise over 15 min and the solution was stirred overnight.
Sodium tert-butoxide (192 mg, 1.94 mmol) was added and the reaction was stirred at 0° C. for 10 minutes.
Methyl iodide (186 μL, 2.98 mmol) was added and the reaction was stirred for 1 h.
The reaction mixture was then partitioned between 1N HCl (50 mL) and EtOAc (75 mL).
The organic layer was washed with 1 N HCl and brine, dried over Na2SO4 and concentrated to yield 2-methyl-2-(4-nitrophenyl)propanenitrile as a green waxy solid (1.25 g, 99percent).
1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=8.9 Hz, 2H), 7.66 (d, J=8.9 Hz, 2H), 1.77 (s, 6H).
83% With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 8 h; To a suspension of 4-nitrophenylacetonitrile 1 (1.0 equiv, 4.50 g, 27.8 mmol), tetrabutyl ammonium bromide (TBAB, 0.448 g, 1.39 mmol, 0.05 equiv) and iodomethane (11.8 g, 83.4 mmol, 3.0 equiv) in dichloromethane (DCM, 40.0 mL) was added sodium hydroxide (2.78 g, 69.5 mmol, 2.5 equiv) in water (40.0 mL) dropwise.
After stirring at room temperature for 8 h, the organic layer was separated, washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuo.
Then the residue was subjected to flash column chromatography using EA/PE (1:14-1:7) as eluent to furnish the di-methylated product as a white crystal. Yield: 83percent; ESI-MS: m/z = 191 [M+H]+.
77% With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; The above reaction scheme illustrates the synthesis of a compound of the invention 2-13.Methylation of starting material 2-1 yields compound 2-2,
77% With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; 10556] The above reaction scheme illustrates the synthesis of a compound of the invention 2-13. Methylation of starting material 2-1 yields compound 2-2, which is subsequently reduced to the amine 2-3. In a separate reaction, compound 2-4 is converted to a salt, such as an HC1 salt, which is then reacted, for example, with 2-nitrovinyl-hydroxylamine to yield compound 2-6. Further cyclization yields compound 2-7. Halogenation with a reagent such as POd3 results in compound 2-8, which can be coupled with intermediate 2-3 to yield 2-9. The nitro moiety of 2-9 is subsequently reduced to an amine, and a further reaction with 4-nitrophenyl carbonochloridate results in the heterocycle 2-11. The desired compound 2-13 is then prepared by coupling to the benzoxazolyl boronate 2-12, for example in a Suzuki coupling.
76% With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; 4-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL). The reaction mixture was stirred for 20 hours at RT. The organic layer was separated, was dried over Na2SOzJ, and was evaporated to dryness. The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76 percent); 1H NMR (CDCl3, 300 MHz): δ 8.220-8.250 (d, 2H, J=9Hz), 7.627-7.657 (d, 2H, J=9Hz), 1.750 (s, 6H).
76% With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 20 h; Step 1:
2-Methyl-2-(4-nitrophenyl)propanenitrile
4-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL).
The reaction mixture was stirred for 20 hours at RT.
The organic layer was separated, was dried over Na2SO4, and was evaporated to dryness.
The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76percent); 1H NMR (CDCl3, 300 MHz): δ 8.220-8.250 (d, 2H, J=9 Hz), 7.627-7.657 (d, 2H, J=9 Hz), 1.750 (s, 6H).
68%
Stage #1: With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In dichloromethane; water
Stage #2: at 0 - 20℃; for 12 h;
a) Sodium hydroxide (12.3 g, 0.30 mol) was added to (4-nitrophenyl)-acetonitrile (1O g, 61.7 mml) and tetrabutylammonium hydroxide (6.4 g, 24.7 mmol) in a mixture of DCM (50 mL) and water (12 mL). When a clear solution had formed, it was cooled to 0 0C and iodomethane (70 g, 0.49 mol) was added, then the mixture was warmed to r.t. and stirred for 12h. The mixture was partitioned between water and DCM then the separated organic phase was dried over sodium sulfate and concentrated to obtain the crude product. This was subjected to column chromatography on silica gel (60-120 mesh), eluting with 6percent ethyl acetate/hexane which afforded 2-methyl-2-(4- nitrophenyl)-ρropionitrile (8 g, 68percent).
60% With tetrabutylammomium bromide; sodium hydroxide In dichloromethane at 20℃; for 4 h; 20 g (0.12 mol) of 4-nitrobenzeneacetonitrile,2.2 g (7.4 mmol) of TBAB,In a 500 mL one-necked flask, a solution of 21 mL (0.396 mol) of methyl iodide and 174 mL of dichloromethane was added dropwise over a dropping funnel and 168 mL of a sodium hydroxide solution (1.96 mol / L) was slowly added. Stirred at room temperature for 4h,The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1/3, V: V) The intermediate 415.57g, yield 66 ,
60%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 20℃; for 1.5 h;
To a solution of (4-nitro-phenyl)-acetonitrile (5.00 g; 30.9 mmol) in dry DMF (30 mL) cooled at 0 °C, under N2 atmosphere, was added NaH (60percent dispersion in mineral oil; 1.23 g; 30.9 mmol) portionwise and the mixture was stirred for 15 min at 0°C. Then iodomethane (1.92 mL; 30.9 mmol) was added and the mixture was stirred at room temperature for 1.5 hour. The reaction was re-cooled at 0°C and NaH (60percent dispersion in mineral oil; 1.23 g; 30.9 mmol) was added again portionwise. After stirring at 00C for 15 min, iodomethane (1.92 mL; 30.9 mmol) was added and the reaction was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the residue was taken up with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude was purified by chromatography [SiO2, Petroleum ether/EtOAc (95/5 to 8/2)] to give the title compound as a yellow solid (3.50 g, 60 percent yield). LCMS (RT): 1.42 min (Method A); MS (ES+) gave m/z: 191.1 (MH+).
4.5 g With sodium hydroxide In dichloromethane at 20℃; for 16 h; 2-(4-nitrophenyl)acetonitrile (4.86 g, 30 mmol) was dissolved in 50mL dichloromethane. To the resulting mixture was added dropwise 30mL of an aqueous sodium hydroxide (3.6 g, 90 mmol) solution. Then to the resulting mixture was added dropwise iodomethane (10.65 g, 75 mmol). After the completion of the dropwise addition, the resulting mixture was reacted at room temperature under protection from light for 16 hrs. 50 mL water and 100 mL dichloromethane were added. The phases are separated. The aqueous phase was extracted with 100 mL dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. The resulting crude product is separated by silicagel column chromatography(EtOAc/PE=0-1/20) to obtain a pale yellow solid of 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g).
4.5 g With sodium hydroxide In dichloromethane; water at 20℃; for 16 h; 10206] 2-(4-nitrophenyl)acetonitrile (4.86 g, 30 mmol) was dissolved in SOmE dichioromethane. To the resulting mixture was added dropwise 30 mE of an aqueous sodium hydroxide (3.6 g, 90 mmol) solution. Then to the resulting mixture was added dropwise iodomethane (10.65 g, 75 mmol). Afier the completion of the dropwise addition, the resulting mixture was reacted at room temperature under protection from light for 16 irs. 50 mE water and 100 mE dichloromethane were added. The phases are separated. The aqueous phase was extracted with 100 mE dichioromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. The resulting crude product is separated by silicagel column chromatography (EtOAc/PE=0-i/20) to obtain a pale yellow solid of 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g).

Reference: [1] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0720
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 17, p. 2203 - 2214
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4834 - 4848
[4] Patent: WO2018/208132, 2018, A1, . Location in patent: Paragraph 321-325
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596
[6] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 119
[7] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0555; 0556
[8] Patent: WO2011/1212, 2011, A1, . Location in patent: Page/Page column 38
[9] Patent: US2012/108627, 2012, A1, . Location in patent: Page/Page column 16
[10] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 120
[11] Patent: CN104411706, 2016, B, . Location in patent: Paragraph 0199-0200
[12] Patent: WO2008/117175, 2008, A2, . Location in patent: Page/Page column 98
[13] Patent: WO2006/65646, 2006, A1, . Location in patent: Page/Page column 21-22
[14] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1027 - 1030
[15] Patent: WO2005/54238, 2005, A1, . Location in patent: Page/Page column 99
[16] Patent: WO2008/64093, 2008, A2, . Location in patent: Page/Page column 17-18
[17] Patent: US2011/98311, 2011, A1,
[18] Patent: US2012/108583, 2012, A1, . Location in patent: Page/Page column 29
[19] Patent: WO2013/23119, 2013, A1, . Location in patent: Page/Page column 27; 28
[20] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[21] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 74
[22] Patent: EP2896622, 2015, A1, . Location in patent: Paragraph 0133; 0134
[23] Patent: US2015/239885, 2015, A1, . Location in patent: Paragraph 0205; 0206
[24] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 359
[25] Patent: US9358229, 2016, B2, . Location in patent: Page/Page column 19
[26] Patent: WO2017/156181, 2017, A1, . Location in patent: Paragraph 00439
[27] Patent: WO2006/122806, 2006, A2, . Location in patent: Page/Page column 48; 49
  • 4
  • [ 74-88-4 ]
  • [ 71825-51-9 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 0℃; for 0.5 h;
Stage #2: at 20℃;
40percent sodium hydroxide solution (4ml) was added to tetrabutyl-ammonium iodide (341mg, 0.924mmol) and a solution of (4-nitro-ph.enyl)-acetonitrile (Ig, 6.17rnrnol) in dichloromethane (10ml) under vigorous stirring. After 30 min, the reaction mixture was cooled to O0C and methyl iodide (1.536ml, 24.67mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with dichloromethane and water, the organic layer separated and washed with water, dried and concentrated to oil. The crude compound was purified by column chromatography over silica gel using ethyl acetate/ pet ether (1:9) as eluent to give 2-methyl-2-(4-nitro-phenyl)-propionitrile (0.6g, 51percent).
Reference: [1] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 49-50
  • 5
  • [ 1195-98-8 ]
  • [ 71825-51-9 ]
YieldReaction ConditionsOperation in experiment
73% at 20℃; for 5 h; The 98percent concentrated sulfuric acid 24mL, 65percent concentrated sulfuric acid 16mL, 16g of polyphosphoric acid mixture, was added dropwise at room temperature after the 2-methyl-phenyl-propionitrile (15g, 0.103mol), reaction for 5 hours,, solution was poured into large amount of water, can be seen as a pale yellow solid was precipitated, filtered, and the filter cake was washed with 95percent ethanol, to give a white solid (14.3g, yield 73percent).
Reference: [1] Patent: CN103254203, 2016, B, . Location in patent: Paragraph 0065; 0084; 0085
  • 6
  • [ 71-91-0 ]
  • [ 555-21-5 ]
  • [ 74-88-4 ]
  • [ 71825-51-9 ]
Reference: [1] Patent: US2009/137595, 2009, A1,
  • 7
  • [ 851233-80-2 ]
  • [ 100-00-5 ]
  • [ 71825-51-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
  • 8
  • [ 14500-58-4 ]
  • [ 143-33-9 ]
  • [ 71825-51-9 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 2, p. 196 - 204
  • 9
  • [ 71825-51-9 ]
  • [ 180081-10-1 ]
Reference: [1] Patent: US2011/98311, 2011, A1,
[2] Patent: US2015/231142, 2015, A1,
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Chemical Structure| 288251-96-7

[ 288251-96-7 ]

2-Isobutyl-5-nitrobenzonitrile

Similarity: 0.87

Chemical Structure| 31643-49-9

[ 31643-49-9 ]

4-Nitrophthalonitrile

Similarity: 0.85

Chemical Structure| 619-72-7

[ 619-72-7 ]

4-Nitrobenzonitrile

Similarity: 0.81

Nitroes

Chemical Structure| 621-50-1

[ 621-50-1 ]

2-(3-Nitrophenyl)acetonitrile

Similarity: 0.90

Chemical Structure| 610-66-2

[ 610-66-2 ]

2-(2-Nitrophenyl)acetonitrile

Similarity: 0.88

Chemical Structure| 288251-96-7

[ 288251-96-7 ]

2-Isobutyl-5-nitrobenzonitrile

Similarity: 0.87

Chemical Structure| 31643-49-9

[ 31643-49-9 ]

4-Nitrophthalonitrile

Similarity: 0.85

Chemical Structure| 619-72-7

[ 619-72-7 ]

4-Nitrobenzonitrile

Similarity: 0.81

Nitriles

Chemical Structure| 621-50-1

[ 621-50-1 ]

2-(3-Nitrophenyl)acetonitrile

Similarity: 0.90

Chemical Structure| 610-66-2

[ 610-66-2 ]

2-(2-Nitrophenyl)acetonitrile

Similarity: 0.88

Chemical Structure| 288251-96-7

[ 288251-96-7 ]

2-Isobutyl-5-nitrobenzonitrile

Similarity: 0.87

Chemical Structure| 31643-49-9

[ 31643-49-9 ]

4-Nitrophthalonitrile

Similarity: 0.85

Chemical Structure| 619-72-7

[ 619-72-7 ]

4-Nitrobenzonitrile

Similarity: 0.81