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Product Details of [ 635-46-1 ]

CAS No. :635-46-1 MDL No. :MFCD00006693
Formula : C9H11N Boiling Point : -
Linear Structure Formula :- InChI Key :LBUJPTNKIBCYBY-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :69460
Synonyms :

Calculated chemistry of [ 635-46-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.34
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 2.29
Log Po/w (WLOGP) : 1.47
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.52
Consensus Log Po/w : 2.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.373 mg/ml ; 0.0028 mol/l
Class : Soluble
Log S (Ali) : -2.18
Solubility : 0.88 mg/ml ; 0.0066 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.0759 mg/ml ; 0.00057 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 635-46-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 635-46-1 ]

* 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 [ 635-46-1 ]
  • Downstream synthetic route of [ 635-46-1 ]

[ 635-46-1 ] Synthesis Path-Upstream   1~36

  • 1
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  • [ 22358-80-1 ]
  • [ 3973-08-8 ]
Reference: [1] Helvetica Chimica Acta, 1948, vol. 31, p. 924,925
  • 2
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  • [ 5332-25-2 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[2] Tetrahedron, 2017, vol. 73, # 36, p. 5389 - 5396
[3] Arkivoc, 2018, vol. 2018, # 3, p. 362 - 374
  • 3
  • [ 635-46-1 ]
  • [ 580-19-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
[2] Patent: US9522908, 2016, B2,
  • 4
  • [ 635-46-1 ]
  • [ 58196-33-1 ]
  • [ 61468-43-7 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 38, p. 4565 - 4568
  • 5
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  • [ 49716-18-9 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[2] Molecular Catalysis, 2018, vol. 452, p. 145 - 153
  • 6
  • [ 612-57-7 ]
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  • [ 767-92-0 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 9, p. 5816 - 5822
  • 7
  • [ 612-57-7 ]
  • [ 91-22-5 ]
  • [ 635-46-1 ]
  • [ 49716-18-9 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[2] Journal of Materials Chemistry A, 2017, vol. 5, # 7, p. 3260 - 3266
  • 8
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  • [ 90562-36-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5119 - 5123
  • 9
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  • [ 22190-35-8 ]
YieldReaction ConditionsOperation in experiment
35% With N-Bromosuccinimide In tetrachloromethane at 0℃; for 3 h; NBS (28 g, 158 mmol) was added to a solution of 1,2,3,4-tetrahydroquinoline (20 g, 150.16 mmol) in carbon tetrachloride (200 mL). The resulting solution was stirred for 3 h at 0°C, extracted with dichloromethane(3 x 50 mL) and concentrated in vacuo to give a residue, which was applied onto a silica gel column with 1 percent ethyl acetate in petroleum ether to give 6-bromo- 1 ,2,3,4-tetrahydroquinoline as a yellow solid (11 g, 35percent).LC/MS(ES, m/z):[M+H]+ 212.1'H-NMR (300 MHz, CDC13) δ 7.03 - 7.07 (m, 2H), 6.35 - 6.38 (m, 1H), 3.51 - 3.55 (m, 2H), 2.73- 2.80 (m, 2H), 1.89 - 1.99 (m, 2H)
20 g With N-Bromosuccinimide In acetonitrile at 0℃; for 4 h; Reaction step 1
Synthesis of 6-bromo-1,2,3,4-tetrahydroquinoline
To a stirred solution of 1,2,3,4-tetrahydroquinoline (20.0 g, 150 mmol, 1.0 eq) in acetonitrile, N-bromosuccinimide (25.5 g, 143 mmol, 0.95 eq) was added in four equal portions at 0° C., in an interval of 20 min between each portion.
Stirring was continued at 0° C. for 3 h.
After completion of the reaction (monitored by TLC, 10percent ethyl acetate-hexane, Rf=0.55), diethyl ether was added and the mixture was washed with saturated sodium bicarbonate solution followed by water and brine.
The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure.
The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with 5percent ethyl acetate in hexanes to obtain 6-bromo-1,2,3,4-tetrahydroquinoline (20.0 g, 64percent) as yellow oil. LCMS: Purity: 92.25percent (ES+): m/z 212.0 (M+H+); tr=2.06 min.
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
[2] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 60
[3] Patent: US2008/221160, 2008, A1, . Location in patent: Page/Page column 11; 12
[4] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 11
[5] Patent: WO2013/166015, 2013, A1, . Location in patent: Paragraph 0093 - 0095
[6] Patent: US2015/252022, 2015, A1, . Location in patent: Paragraph 0374
[7] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[8] Tetrahedron, 2017, vol. 73, # 36, p. 5389 - 5396
[9] Patent: US2016/24056, 2016, A1, . Location in patent: Paragraph 0243
  • 10
  • [ 5332-25-2 ]
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  • [ 22190-35-8 ]
Reference: [1] Synlett, 2004, # 15, p. 2827 - 2829
  • 11
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  • [ 22190-35-8 ]
  • [ 190843-73-3 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 43, p. 10068 - 10074
  • 12
  • [ 635-46-1 ]
  • [ 6640-50-2 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 21, p. 6799 - 6803
  • 13
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  • [ 50488-36-3 ]
  • [ 103028-32-6 ]
Reference: [1] Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 896 - 908
  • 14
  • [ 635-46-1 ]
  • [ 613-51-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
[2] Inorganic Chemistry, 2014, vol. 53, # 11, p. 5637 - 5646
[3] Patent: US9522908, 2016, B2,
  • 15
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  • [ 504-63-2 ]
  • [ 479-59-4 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 7, p. 1090 - 1096
  • 16
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  • [ 504-63-2 ]
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Reference: [1] ChemCatChem, 2015, vol. 7, # 7, p. 1090 - 1096
  • 17
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  • [ 479-59-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 5, p. 1048 - 1056
  • 18
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  • [ 109-70-6 ]
  • [ 479-59-4 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 30, p. 6100 - 6109
[2] Chemische Berichte, 1892, vol. 25, p. 2802
  • 19
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  • [ 70173-54-5 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 30, p. 6100 - 6109
  • 20
  • [ 635-46-1 ]
  • [ 5382-49-0 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
  • 21
  • [ 635-46-1 ]
  • [ 98203-04-4 ]
Reference: [1] Arkivoc, 2018, vol. 2018, # 3, p. 362 - 374
  • 22
  • [ 635-46-1 ]
  • [ 30450-62-5 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at -10 - 10℃; for 3.5 h;
Stage #2: With sodium carbonate In water at 0℃;
Concentrated sulfuric acid (30.00 mL) was cooled to -10° C. with an ice/salt bath.
To this, 1,2,3,4-tetrahydro-quinoline (10.60 g, 75.60 mmol) and a solution of nitric acid (99.5percent, 4.80 g, 75.60 mmol) in sulfuric acid (15.00 mL) were added simultaneously within 1 hour, so that the temperature of the reaction mixture does not exceed 10° C.
The mixture was stirred then for 2.5 hours at -5° C., then poured over ice and treated with sodium carbonate (0.10 kg) until pH 8-9 was reached.
The solid was filtered, washing with water, then dissolved in dichloromethane.
The organic phase was washed with water, dried over magnesium sulphate and evaporated.
7-Nitro-1,2,3,4-tetrahydro-quinoline was obtained as a viscous brown oil, 13.70 g (85percent), 84percent purity.
59%
Stage #1: at -10℃; for 0.5 h;
Stage #2: at -10 - -5℃; for 3 h;
1,2,3,4-Tetrahydroquinoline (26.8 g, 0.2 mol) was dissolved in 75 mL of 96.6percent sulfuric acid and cooled in a salt-ice bath to -10° C.
After stirring for 30 min, 9.5 mL (0.2 mol) of 90percent nitric acid in 40 mL of sulfuric acid was added at such a rate that the temperature remained at -5 to -10° C.
The reaction mixture was stirred in the ice bath for 3 hr and then poured onto ice.
The solution was neutralized to pH 8 with sodium carbonate and the precipitate was filtered, washed with water, and dried to provide the title compound in crude form, which was purified by column chromatography using a hexanes:ethyl acetate gradient (0-30percent) to provide the title compound in pure form as an orange solid (21.4 g, 59percent yield).
51% at 0℃; 7-aminoquinoline was prepared according to the following reaction in scheme 14.
25% With KNO3 In sulfuric acid Example 1
7-Nitro-1,2,3,4-tetrahydro-quinoline
To a mixture of 1,2,3,4-tetrahydro-quinoline (20.0 g, 0.15 mol) dissolved in H2SO4 (98percent, 150 mL), KNO3 (18.2 g, 0.18 mol) was slowly added at 0° C.
The reaction was allowed to warm to room temperature and stirred over night.
The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 8.
After extraction with CH2Cl2, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated.
The residue was purified by column chromatography (petroleum ether-EtOAc, 10:1) to give 7-nitro-1,2,3,4-tetrahydro-quinoline (6.6 g, 25percent).
25% at 0 - 20℃; To a mixture of 1,2,3,4-tetrahydro-quinoline (20.0 g, 0.15 mol) dissolved in H2SO4 (98percent, 150 mL), KNO3 (18.2 g, 0.18 mol) was slowly added at 0° C.
The reaction was allowed to warm to room temperature and stirred over night.
The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 8.
After extraction with CH2Cl2, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated.
The residue was purified by column chromatography (petroleum ether-EtOAc, 10:1) to give 7-nitro-1,2,3,4-tetrahydro-quinoline (6.6 g, 25percent).
61% With nitric acid; sodium hydrogencarbonate In sulfuric acid 7-Nitro-1,2,3,4-tetrahydroquinoline
1,2,3,4-Tetrahydroquinoline (5 g, 0.0375 mol) was dissolved in 16 mL of sulfuric acid and the temperature lowered to 0° C., then 90percent fuming nitric acid (1.67 mL, 0.0375 mol) was added slowly and the mixture stirred at 0° C. for 30 min.
It was then poured onto 100 g of ice and extracted with dichloromethane (2*100 mL).
The organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 4.1 g (61percent) of 7-nitro-1,2,3,4-tetrahydroquinoline.
61% With nitric acid; sodium hydrogencarbonate In sulfuric acid 7-Nitro-1,2,3,4-tetrahydroquinoline.
1,2,3,4-Tetrahydroquinoline (5 g, 0.0375 mol) was dissolved in 16 mL of sulfuric acid and the temperature lowered to 0° C., then 90percent fuming nitric acid (1.67 mL, 0.0375 mol) was added slowly and the mixture strirred at 0° C. for 30 min.
It was then poured onto 100 g of ice and extracted with dichloromethylane (2*100 mL).
The organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL) and concentrated in vacuo to a reddish residue.
that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 4.1 g (61percent) of 7-nitro-1,2,3,4-tetrahydroquinoline.
Data for 7-nitro-1,2,3,4-tetrahydroquinoline: 1 H NMR (400 MHz, CDCl3) 7.39 (dd, J=8.3, 2.2, 1H), 7.26 (d, J=3.5, 1H), 7.01 (d, J=8.3, 1H), 4.16 (bs, 1H), 3.35 (t, J=5.0, 2H), 2.8 (t, J=6.3, 2H), 1.95 (quintet, J=6.1, 2H).
61% With nitric acid; sodium hydrogencarbonate In sulfuric acid 7-Nitro-1,2,3,4-tetrahydroquinoline.
1,2,3,4-Tetrahydroquinoline (5 g, 0.0375 mol) was dissolved in 16 mL of sulfuric acid and the temperature lowered to 0° C., then 90percent fuming nitric acid (1.67 mL, 0.0375 mol) was added slowly and the mixture stirred at 0° C. for 30 min.
It was then poured onto 100 g of ice and extracted with dichloromethane (2*100 mL).
The organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 4.1 g (61percent) of 7-nitro-1,2,3,4-tetrahydroquinoline.
61% With nitric acid; sodium hydrogencarbonate In sulfuric acid 7-Nitro-1,2,3,4-tetrahydroquinoline
1,2,3,4-Tetrahydroquinoline (5 g, 0.0375 mol) was dissolved in 16 mL of sulfuric acid and the temperature lowered to 0° C., then 90percent fuming nitric acid (1.67 mL, 0.0375 mol) was added slowly and the mixture strirred at 0° C. for 30 min.
It was then poured onto 100 g of ice and extracted with dichloromethane (2*100 mL).
The organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 4.1 g (61percent) of 7-nitro-1,2,3,4-tetrahydroquinoline.

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[2] Patent: US9512111, 2016, B2, . Location in patent: Page/Page column 93; 94
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[4] Chemistry - A European Journal, 2008, vol. 14, # 6, p. 1784 - 1792
[5] European Journal of Organic Chemistry, 2010, # 19, p. 3593 - 3610
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  • 23
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  • [ 30450-62-5 ]
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Reference: [1] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
  • 25
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  • [ 14026-45-0 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
[2] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
[3] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
[4] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
[5] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
[6] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
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[8] Patent: KR101576386, 2015, B1,
  • 26
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Reference: [1] European Journal of Organic Chemistry, 2011, # 8, p. 1504 - 1513
  • 27
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  • [ 50741-36-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
[2] Patent: WO2012/94462, 2012, A2,
  • 28
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  • [ 545-06-2 ]
  • [ 50741-37-2 ]
YieldReaction ConditionsOperation in experiment
68% With boron trichloride; potassium carbonate In methanol; dichloromethane; toluene EXAMPLE 74
To a solution of 1.33 g of 1,2,3,4-tetrahydroquinoline in 10 ml of toluene was added 5.5 ml of a solution of 2.02M of boron trichloride in toluene under ice-cooling.
The mixture was refluxed on an oil bath for 1 hr. and evaporated under atmospheric pressure to remove the toluene.
The residue was mixed with 2 ml of trichloroacetonitrile and heated at 60°-62° C. on an oil bath for 20 hr.
The reaction mixture was dissolved in 20 ml of methylene chloride and poured into a mixture of 9.1 g of potassium carbonate and 40 ml of methanol under ice-cooling.
The mixture was refluxed on an oil bath for 1 hr. and filtered to remove the insoluble material.
The filtrate was concentrated and partitioned between water and methylene chloride.
The methylene chloride layer was washed with dilute HCl, dried over anhydrous magnesium sulfate and concentrated to remove the solvent.
The residue (1.53 g) was purified on a Lobar column and the product (1.10 g) from the methylene chloride elude was recrystallized from ether-n-hexane to give 1.07 g of 8-cyano-1,2,3,4-tetrahydroquinoline as crystals melting at 75°-76° C.
Yield: 68percent
Reference: [1] Patent: US4774331, 1988, A,
[2] Synthetic Communications, 1990, vol. 20, # 1, p. 71 - 84
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  • [ 50741-37-2 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 1, p. 71 - 84
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  • [ 90562-36-0 ]
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  • 31
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  • [ 24424-99-5 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
13% With dmap; triethylamine In acetonitrile at 20 - 55℃; Di-tert-butyl dicarbonate (1.181 g, 5.4 mmol) was added to a solution of 1,2,3, 4-tetrahydroquino line (626 mg, 4.7 mmol), triethylamine (1.3 mL, 9.3 mmol) and DMAP (112 mg, 0.19 mmol) in CH3CN (15 mL). The reaction was stirred for 1.5 h at room temperature and then was heated overnight at 55 °C. The solution was allowed to cool to room temperature and then was evaporated. The residue was partitioned between 25 mL ethyl acetate and 25 mL 1 M HCl. The ethyl acetate solution was further washed with 1 M HCl (2 x 25 mL) and 25 mL brine and then was dried (Na2S04), filtered and evaporated. Purification of the residue by flash chromatography on silica gel using a Combiflash unit by Teledyne Isco (0percent ethyl acetate/hexanes -> 40percent) gave the title compound (139 mg, 13percent).
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 36, p. 12891 - 12903
[2] Patent: WO2015/48553, 2015, A1, . Location in patent: Page/Page column 15; 32
[3] Tetrahedron, 2015, vol. 71, # 29, p. 4738 - 4744
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1971 - 1975
[5] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8051 - 8055
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[4] Patent: EP2143724, 2010, A1, . Location in patent: Page/Page column 24-25
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[2] Patent: US2015/231142, 2015, A1,
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  • [ 905854-03-7 ]
  • [ 905854-02-6 ]
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[2] Patent: US2015/328208, 2015, A1,
[3] Patent: US2015/328208, 2015, A1,
[4] Patent: US2015/328208, 2015, A1,
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Chemical Structure| 491-34-9

[ 491-34-9 ]

1-Methyl-1,2,3,4-tetrahydroquinoline

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