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[ CAS No. 611-34-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 611-34-7
Chemical Structure| 611-34-7
Chemical Structure| 611-34-7
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Product Citations

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. DOI: PubMed ID:

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

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Product Details of [ 611-34-7 ]

CAS No. :611-34-7 MDL No. :MFCD00006797
Formula : C9H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XMIAFAKRAAMSGX-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :11911
Synonyms :

Calculated chemistry of [ 611-34-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.15
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.38
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.05 mg/ml ; 0.00729 mol/l
Class : Soluble
Log S (Ali) : -1.57
Solubility : 3.86 mg/ml ; 0.0268 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0693 mg/ml ; 0.000481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 611-34-7 ]

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

Application In Synthesis of [ 611-34-7 ]

* 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 [ 611-34-7 ]
  • Downstream synthetic route of [ 611-34-7 ]

[ 611-34-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 607-34-1 ]
  • [ 613-51-4 ]
  • [ 580-19-8 ]
  • [ 611-34-7 ]
Reference: [1] Patent: US6750348, 2004, B1, . Location in patent: Page column 41-42
  • 2
  • [ 611-34-7 ]
  • [ 578-67-6 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With sodium hydrogen sulfate In water for 36 h; Reflux
Stage #2: for 8 h; Reflux
5-(2,2,2-Trifluoroethoxy)quinoline (I-E)
To a stirred solution of amine 5-aminoquinoline (5.0 g, 34.67 mmol) in H2O (100 mL) was added sodium bisulfate (NaHSO3; 25.2 g, 242.1 mmol) at RT, and the mixture was stirred at reflux temperature for 36 h.
The resulting solution was cooled to RT, NaOH (9.7 g, 242.5 mmol) was added, and the mixture was stirred at reflux temperature for 8 h.
After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT and the pH was adjusted to 7.0 with 6 Normal (N) hydrochloride acid (HCl).
The precipitate was filtered, washed with H2O, and dried under high vacuum to obtain the desired alcohol M (3.2 g, 22.04 mmol, 64percent) as pale-yellow solid. 1H NMR (500 MHz, CDCl3): δ 8.92 (s, 1H), 8.58 (d, J=8.5 Hz, 1H), 7.71 (d, J=8.5 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.41 (dd, J=8.5, 4.5 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 6.10 (br s, 1H). MS (ESI): m/z 146 [M+H]+.
56% With sulfuric acid; acetic acid; sodium nitrite In water at 0℃; for 5.5 h; Inert atmosphere; Reflux 5-aminoquinoline (15.0 g, 104.0 mmol) was dissolved in a solvent of acetic acid / water / sulfuric acid (8: 1: 1, v / v / v, 130 mL) under an argon atmosphere, and a solution of sodium nitrite (8.6 g, 124.8 mmol) dissolved therein. After the reaction mixture was stirred at 0 °C for 30 minutes, 10percent sulfuric acid solution (780 mL) was boiled, slowly added to the reaction solution, The mixture was refluxed for 5 hours, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 2: 1). The reaction mixture was cooled to room temperature, and a saturated solution of sodium hydrogencarbonate (250 mL) was added thereto, followed by extraction with ethyl acetate (10 X 400 mL). The organic solvent layer was washed with a saturated solution of sodium chloride (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The concentrate was separated and purified by column chromatography (hexane: ethyl acetate = 2: 1) to obtain the desired compound (8.5 g, 56percent yield).
Reference: [1] Patent: US2012/329802, 2012, A1, . Location in patent: Page/Page column 25-26
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[3] Patent: KR101778938, 2017, B1, . Location in patent: Paragraph 0147-0148; 0155; 0160-0162
[4] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 431
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 1562
[6] Monatshefte fuer Chemie, 1884, vol. 5, p. 532
[7] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 431
  • 3
  • [ 611-34-7 ]
  • [ 394-69-4 ]
YieldReaction ConditionsOperation in experiment
55% at 0℃; for 1 h; Preparation LIII 5-fluoro-1,2,3,4-tetrahydroquinoline [0363] 5-fluoroquinoline [0364] To a suspension of 5-aminoquinoline (50 g, 347 mmol) in 48percent HBF4 (200 mL) at 0° C. was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1:1 ethyl acetate/diethyl ether (500 mL). The resulting suspension was filtered and the solid dried. This solid (82.5 g, 338 mmol) was added portionwise to refluxing xylene (1 L) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue dissolved in 1N hydrochloric acid (600 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (10.x.500 mL). The extracts were dried over sodium sulfate, filtered and the volatiles removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10-20percent diethyl ether in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 28.1 g (55percent) of the desired compound. MS (EI, m/z) C9H6FN (M+1) 148.0 [0365] Reduction [0366] A mixture of 5-fluoroquinoline (28.1 g), 5percent palladium on carbon (5.6 g) in methanol was shaken over night at 40° C. under 60 psi hydrogen. The mixture was filtered through celite and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 22.5 g (78percent) of the title compound. [0367] MS (EI, m/z) C9H10FN (M+1) 152.0
24.5% With tetrafluoroboric acid; sodium nitrite In xylene at 0℃; Reflux To a suspension of 5-aminoquinoline (lO.Og, 0.069 mol) in 48percent HBF4 (40 mL) at 0°C was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate/diethyl ether (50 mL). The resulting suspension was filtered and the solid dried. This solid was added portionwise to refluxing xylene (80 mL) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue was dissolved in IN aqueous hydrochloric acid (100 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (3 x 80 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel column chromatography, eluting with 2percent ethyl acetate in petroleum ether to afford 5-fluoroquinoline as a colorless oil (2.5 g, 24.5percent).'H-NMR (300 MHz, CDC13) δ 8.93 - 8.98 (m, 1H), 8.43 - 8.46 (m, H), 7.92 (d, / = 8.4 Hz, 1H), 7.62 - 7.78 (m, 1H), 7.41 - 7.49 (m, 1H), 7.22 - 7.26 (m, 1H)
800 mg at 0℃; for 1 h; To a solution of quinolin-5 -amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0°C was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in IN HC1 (50 mL). After neutralization with NaHC03, the mixture was extracted with ethyl acetate (3 x 50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+
800 mg at 0℃; for 1 h; To a solution of quinolin-5-amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0° C. was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1:1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in 1N HCl (50 mL). After neutralization with NaHCO3, the mixture was extracted with ethyl acetate (3×50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+
800 mg at 0℃; for 1 h; To a solution of quinolin-5 -amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0°C was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in IN HC1 (50 mL). After neutralization with NaHC03, the mixture was extracted with ethyl acetate (3 x 50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+

Reference: [1] Patent: US2003/229026, 2003, A1, . Location in patent: Page 25
[2] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[3] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 75
[4] Biological and Pharmaceutical Bulletin, 1997, vol. 20, # 6, p. 646 - 650
[5] Patent: WO2014/139144, 2014, A1, . Location in patent: Page/Page column 179
[6] Patent: US2014/288081, 2014, A1, . Location in patent: Paragraph 0738; 0739
[7] Patent: WO2014/139325, 2014, A1, . Location in patent: Page/Page column 192; 193
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 6998 - 7011
  • 4
  • [ 611-34-7 ]
  • [ 635-27-8 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: With hydrogenchloride; copper(l) chloride In water at 20℃; for 24 h; Inert atmosphere
To a suspension of 5-aminoquinoline (756 mg, 5.24 mmol) in aqueous 2 N HCl (31 mL) cooled to 0 °C was added a solution of NaNO2 (470 mg, 6.80 mmol) in H2O (14 mL). The reaction mixture was stirred at 0 °C for 30 min and a solution of CuCl (644 mg, 6.51 mmol) in conc. HCl (16 mL) was added. The mixture was allowed to warm to room temperature and stirred for additional 24 h. Saturated NaHCO3 was slowly added to the mixture until no gas was generated. The organic phase was extracted with CH2Cl2 (3 x 50 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (EtOAc/hexane = 1:1) to give 5-chloroquinoline 2d (579 mg, 68percent)
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[3] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 235
  • 5
  • [ 611-34-7 ]
  • [ 4964-71-0 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 0.0833333 h;
Stage #2: With hydrogen bromide; copper(I) bromide In water at 20 - 75℃; for 2 h;
Stage #3: With sodium hydroxide In water
PREPARATION 7
5-Bromoquinoline
Quinolin-5-amine (3.37 g, 23.38 mmol) was dissolved in 9 ml of water and 11 ml of hydrogen bromide (48percent in water); the resulting solution was cooled at 0°C. Sodium nitrite (1.94 g, 28.12 mmol) dissolved in 9 ml of water was dropwise added.
The resultant solution was stirred at room temperature for 5 minutes.
This solution was dropwise added to a solution of copper(I) bromide (4.02 g, 28.02 mmol) in 23 mL of HBr (48percent in water) at 75°C.
The resulting mixture was stirred at room temperature for 2 h.
Then the reaction mixture was basified with sodium hydroxide and extracted twice with ethyl acetate.
The organic phase is washed with brine, filtered and dried over sodium sulfate.
After filtration and evaporation of the solvent, 2.98 g (61 percent) of the final product were obtained.
1H NMR (CDCl3) δ ppm: 7.44 - 7.63 (m, 2 H) 7.84 (d, J=7.42 Hz, 1 H) 8.10 (d, J=8.24 Hz, 1 H) 8.56 (d, J=8.51 Hz, 1 H) 8.94 (br.s., 1H) HPLC/MS (9 min) retention time 5.68 min.
LRMS: m/z 208 (M)/21 0 (M+2)
35%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: With copper(I) bromide In water at 20℃; for 3 h; Inert atmosphere
To a suspension of 5-aminoquinoline (2.11 g, 14.7 mmol) in aqueous HBr (8.6 mL, 48percent in H2O) cooled to 0 °C was added a solution of NaNO2 (2.58 g, 37.5 mmol) in H2O (35 mL). The reaction mixture was stirred at 0 °C for 30 min and a solution of CuBr (2.58 g, 17.6 mmol) in H2O (29 mL) was added. The mixture was allowed to warm to room temperature and stirred for additional 3 h. 4 N NaOH was slowly added to the mixture until pH reached to about 10. The organic phase was extracted with EtOAc (3 x 75 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (EtOAc/hexane = 1:1) to give 5-bromoquinoline 2e (1.08 g, 35percent)
80% With sodium nitrite In water; hydrogen bromide 5-Bromo-quinoline
Sodium nitrite (2.5 g, 41.8 mmol) was dissolved in 15 mL water.
Copper (I) bromide (6.0 g, 41.8 mmol) was dissolved in 38 mL of 48percent HBr and heated to 75° C. The 5-aminoquinoline (5.0 g, 34.7 mmol) was suspended in 15 mL water and 18 mL 48percent HBr and cooled to 0° C.
The sodium nitrite solution was added to the 5-aminoquinoline solution at 0° C.
The resulting diazonium solution was added slowly to the warmed CuBr solution.
The reaction mixture was stirred at room temperature for 2 hr.
The reaction mixture was basified with sodium hydroxide, then filtered through celite.
The solid was washed with methylene chloride, and the aqueous material was extracted with methylene chloride.
The organic layers were combined, dried with Na2SO4, and concentrated in vacuo.
The crude product was chromatographed with 2:1 hexane/ethyl acetate to yield 5.7 g (80percent) of 5-bromo-quinoline as a yellow oil. MS (APCI) m/z 208.0 (M+1).
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[2] Patent: EP2394998, 2011, A1, . Location in patent: Page/Page column 16
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 10, p. 905 - 913
[5] Patent: US2003/96826, 2003, A1,
[6] Patent: US2002/6923, 2002, A1,
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  • [ 611-34-7 ]
  • [ 10470-83-4 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 34, p. 4871 - 4872
[2] Tetrahedron Letters, 1990, vol. 31, # 34, p. 4871 - 4872
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  • [ 6931-19-7 ]
Reference: [1] Patent: KR101778938, 2017, B1,
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  • [ 611-34-7 ]
  • [ 59412-12-3 ]
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
  • 9
  • [ 611-34-7 ]
  • [ 160893-07-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[2] Patent: KR101778938, 2017, B1,
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  • [ 611-34-7 ]
  • [ 160893-04-9 ]
Reference: [1] Patent: KR101778938, 2017, B1,
  • 11
  • [ 611-34-7 ]
  • [ 355386-94-6 ]
Reference: [1] Patent: US2002/19527, 2002, A1,
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