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Chemical Structure| 103-89-9
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Product Details of [ 103-89-9 ]

CAS No. :103-89-9 MDL No. :MFCD00008677
Formula : C9H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :YICAMJWHIUMFDI-UHFFFAOYSA-N
M.W : 149.19 Pubchem ID :7684
Synonyms :

Calculated chemistry of [ 103-89-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.72
TPSA : 29.1 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) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 1.84
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.16 mg/ml ; 0.00781 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.77 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.105 mg/ml ; 0.000705 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 103-89-9 ]

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

Application In Synthesis of [ 103-89-9 ]

* 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 [ 103-89-9 ]
  • Downstream synthetic route of [ 103-89-9 ]

[ 103-89-9 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 103-89-9 ]
  • [ 1457-93-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 2
  • [ 103-89-9 ]
  • [ 51-79-6 ]
  • [ 18731-19-6 ]
Reference: [1] Journal of the Indian Chemical Society, 1929, vol. 6, p. 282[2] Chem. Zentralbl., 1929, vol. 100, # II, p. 887
  • 3
  • [ 103-89-9 ]
  • [ 556-08-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 340 - 342[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 2, p. 381 - 384
[3] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3744 - 3747
[4] Kinetics and Catalysis, 2010, vol. 51, # 4, p. 516 - 520
[5] Justus Liebigs Annalen der Chemie, 1921, vol. 423, p. 90,91
[6] Chemische Berichte, 1903, vol. 36, p. 1805
[7] Chemische Berichte, 1885, vol. 18, p. 2942
[8] Chemische Berichte, 1876, vol. 9, p. 1302
[9] Chemische Berichte, 1903, vol. 36, p. 1805
  • 4
  • [ 64-19-7 ]
  • [ 103-89-9 ]
  • [ 66047-05-0 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Russian Journal of Applied Chemistry, 2008, vol. 81, # 7, p. 1198 - 1201
  • 5
  • [ 103-89-9 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Petroleum Chemistry, 2009, vol. 49, # 5, p. 397 - 400
  • 6
  • [ 103-89-9 ]
  • [ 66047-05-0 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Petroleum Chemistry, 2009, vol. 49, # 5, p. 397 - 400
  • 7
  • [ 64-19-7 ]
  • [ 103-89-9 ]
  • [ 556-08-1 ]
Reference: [1] Kinetics and Catalysis, 2010, vol. 51, # 4, p. 516 - 520
  • 8
  • [ 68-12-2 ]
  • [ 103-89-9 ]
  • [ 73568-27-1 ]
YieldReaction ConditionsOperation in experiment
87% at 90℃; for 10 h; Cooling with ice 2) 3.5 ml of DMF and 17 ml of POCl3 were mixed under ice-cooling,After stirring, 2.24 g (15 mmol) of compound 1 was added, and the resulting solution was placed in a reflux apparatus,Heated to 90 ° C for 10 hours, cooled and poured into 500 ml of ice water, and the compound 2(2.7 g, yield 87percent).
87% at 90℃; for 10 h; Cooling with ice 2) 3.5 ml DMF and 17 ml POCl3 are mixed under ice bath, then add 2.24g (15mmol) compound 1, the resulting solution is placed in reflux device, heating to 90 °C reflux for 10 hours, after cooling is poured into 500 ml ice water, filtered to obtain compound 2 (2.7g, yield 87percent).
84.83% With bis(trichloromethyl) carbonate In chloroform at -5 - 51℃; for 6.5 h; Green chemistry This example provides a process for the synthesis of 2-chloro-3-formyl-6-methylquinoline with the following main steps: under ice-salt bath, 3.00g (20.13 mmol) acetanilide, 8.03 g (27.04 mmol) of BTC and 10 mL of trichloromethane 4.2 mL (54.66mmol) DMF was added dropwise over 80 min after the temperature was maintained below -5 °C. The rate of the bubble overflow was controlled by the tail gas uptake rate. After the addition of the DMF, the mixture was stirred continuously for 10 min. For water bath, plus Heat to 51 °C, reaction 5 hours, steaming part of the solvent, adding ice water, 10percent NaOH to adjust the pH to 8 ~ 9, pumping, recrystallization. The yield was 84.83percent.
77% at 0 - 65℃; for 8 h; General procedure: At 0 °C to a stirred solution of POCl3 (39.6 g, 259 mmol) and anhydrous DMF (8 g, 111mmol) was added acetanilide (5 g, 37 mmol). The mixture was then heated to 65 °C and the progress of the reaction was monitored by TLC analysis. After 8 h the reaction mixturewas then cooled to room temperature and added cautiously into ice-cold water. The solid precipitated was collected by filtration to isolate the compound 1a as yellow solid.
66.7% at 0 - 85℃; POCl3 (111 mL, 1.19 mol) was added drop wise to DMF (40 mL, 0.51 mol) at 0 °C, followed by a portion wise addition of N-acetyl-p-toluidine (S2) (25.7 g, 0.17 mol). The resulting mixture was stirred for 30 min at rt and the reaction mixture heated at 85 °C for 6 h. The resulting solution was cooled to rt and slowly poured into ice-water. The resulting precipitate was filtered, washed with water, dried and crystallized from ethyl acetate to give aldehyde (S3) (23.6 g, 66.7percent). 1H NMR (400 MHz, DMSO-d6 ppm): 2.48 (s, 3H), 7.79 (d, 1H), 7.91 (d, 1H), 8.01 (s, 1H), 8.81 (s, 1H), 10.35 (s, 1H). m/z (APCI+) 206 (M+H+). mp 124-125 °C.
64%
Stage #1: at 0℃; for 0.25 h;
Stage #2: for 4 h; Reflux
General procedure: Dimethylformamide (12 mmol, 3 equiv.) was cooled at 0°C in a round flask equipped with a drying tube and phosphorus pentachloride (18 mmol, 4.5 equiv.) was added slowly and the mixture was stirred for 15 minutes keeping the temperature below 0°C. To this solution was added in a portion the corresponding acetanilide (4 mmol, 1 equiv.) and the reaction mixture was heated under reflux and stirring for the appropiate time depending of the acetanilide. The resulted mixture was cooled to 0°C and the solution was poured slowly into ice-water and stirring for ten minutes, obtaining a yellow solid which was filtered, washed several time with cold water and dried under vacuum. The 2-chloroquinoline-3-carbaldehydes were recrystallized according to the literature.
34%
Stage #1: at 0℃; Heating / reflux
Stage #2: at 0℃;
Step 2:
2-Chloro-6-methylquinoline-3-carbaldehyde
Phosphoryl trichloride (237.2 g, 1.55 mol) was added dropwise with stirring, while cooling to 0° C. to N,N-dimethylformamide (40.4 g, 552.74 mmol). N-p-Tolylacetamide (33 g, 221.19 mmol) was then added and the resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux.
The reaction mixture was then quenched by the adding 3000 ml of H2O/ice.
Adjustment of the pH to 9 was accomplished by the addition of Na2CO3.
The resulting solution was extracted with DCM (3*3000 mL).
The organics were combined, dried over MgSO4, and concentrated by evaporation under vacuum using a rotary evaporator.
The residue was purified by column chromatography on silica gel eluding with a 1:10 EtOAc:hexanes to afford 15.3 g (34percent) of 2-chloro-6-methylquinoline-3-carbaldehyde as a yellow solid. LCMS: 206 (M+H)+.

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[10] Asian Journal of Chemistry, 2015, vol. 27, # 10, p. 3667 - 3670
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[12] Tetrahedron Letters, 2006, vol. 47, # 44, p. 7779 - 7782
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  • 9
  • [ 103-89-9 ]
  • [ 73568-27-1 ]
YieldReaction ConditionsOperation in experiment
87% for 10 h; Reflux General procedure: To the prepared TCTA–DMFreagent, 9.8 mmol of the Acetanilide was added and stirred under refluxconditions. Progress of the reaction was checked by TLC till the completion ofthe reaction. Analytical TLC was carried out using Merck aluminum-backed0.2 mm silica gel 60 F-254 plates. Column chromatography was conductedusing Merck silica gel 60 (230–400 mesh). After completion of the reaction,water was added to the reaction mixture and stirred for a few more minutes toextract inorganic components into water. The organic layer was separated andthe crude product thus obtained was further purified with columnchromatography (silica gel, ethyl acetate/n-hexane)
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 37, p. 5164 - 5167
  • 10
  • [ 68-12-2 ]
  • [ 103-89-9 ]
  • [ 73568-27-1 ]
  • [ 7549-96-4 ]
  • [ 78708-02-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 1520 - 1530
  • 11
  • [ 103-89-9 ]
  • [ 60956-23-2 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 514
[2] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 153[3] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 202
  • 12
  • [ 103-89-9 ]
  • [ 71838-16-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 153[2] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 202
  • 13
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  • [ 6627-51-6 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2103,2106
  • 14
  • [ 103-89-9 ]
  • [ 56461-98-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 139, p. 296,305
  • 15
  • [ 103-89-9 ]
  • [ 326-67-0 ]
YieldReaction ConditionsOperation in experiment
13% With Selectfluor; sodium chloride In water for 24 h; Reflux 1a as example: To a stirred suspension of N-(p-tolyl)acetamide 1a (75 mg, 0.5 mmol) and Selectfluor (213 mg, 0.6 mmol) in water (3.0 mL) was added HBr (40percent aqueous, 0.08 mL, 0.55 mmol), and the mixture was stirred for 5 min at room temperature. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (2.0 mL) and water (20.0 mL), and extracted with CH2Cl2 (10.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether–ethyl acetate = 6:1, v/v) to afford N-(2-bromo-4-methylphenyl)acetamide 2a as a white solid (108 mg, 95percent yield).
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[3] Green Chemistry, 2017, vol. 19, # 14, p. 3344 - 3349
[4] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5390 - 5394
  • 16
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  • [ 6973-09-7 ]
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 6, p. 671 - 677
  • 17
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  • [ 70733-25-4 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 4, p. 294 - 295
  • 18
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  • [ 101580-70-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 153[2] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 202
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