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Product Details of [ 93-60-7 ]

CAS No. :93-60-7 MDL No. :MFCD00006388
Formula : C7H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YNBADRVTZLEFNH-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :7151
Synonyms :
Nicotinic acid methyl ester
Chemical Name :3-(Methoxycarbonyl)pyridine

Calculated chemistry of [ 93-60-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.52
TPSA : 39.19 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) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 0.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.53
Solubility : 4.09 mg/ml ; 0.0298 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 7.97 mg/ml ; 0.0581 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.16 mg/ml ; 0.00849 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 93-60-7 ]

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

Application In Synthesis of [ 93-60-7 ]

* 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 [ 93-60-7 ]
  • Downstream synthetic route of [ 93-60-7 ]

[ 93-60-7 ] Synthesis Path-Upstream   1~32

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Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, p. 1204
[2] Journal of the American Chemical Society, 1927, vol. 49, p. 1312
  • 2
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  • [ 149246-87-7 ]
Reference: [1] Patent: WO2015/97122, 2015, A1,
  • 3
  • [ 93-60-7 ]
  • [ 498-95-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In water at 120℃; for 1 h; To 0.25 g methyl nicotinate in 40 ml of H20, HRO/Na-β catalyst (50 mg) was added in areactor vessel. The reactor vessel was then heated at 120 °C for 1 h under H2 pressure (15bar). After completion of the reaction, the catalyst was separated by using centrifuge and theobtained clear product mixture was analyzed by GC-MS. The reaction gave 100percent conversion of aniline with 100percent yield of piperidine-3-carboxylic acid.
Reference: [1] Patent: WO2017/60922, 2017, A1, . Location in patent: Page/Page column 15; 22
  • 4
  • [ 93-60-7 ]
  • [ 100-55-0 ]
YieldReaction ConditionsOperation in experiment
95% With C18H28Br2N4Ru; potassium <i>tert</i>-butylate; hydrogen In 1,4-dioxane at 105℃; for 8 h; General procedure: To a mixture of catalyst (0.01 mmol), KOtBu (10 mol percent), and 1,4-dioxane (4.0 mL) in a Parr high-pressure reactor was added the ester(1.0 mmol). The dark red solution was purged with H2 and stirred under 400 psi of H2 at 105 °C for 8 h. Products isolation were performed via column chromatography using silica gel as stationary phase and n-pentane/ethylacetate or n-pentane/isopropanol mixture as eluent. The products were confirmed by 1H NMR.
60.5% With hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In isopropyl alcohol at 150℃; for 24 h; In an autoclave, the reactant and Ru(acac)3 were dissolved with 1.4 equivalents of tris(diphenylphosphinomethyl)ethane in isopropanol, and converted at 150° C. and 150 bar of hydrogen pressure for 24 h. After the reaction, the reaction mixture was analyzed by gas chromatography.Conversion, selectivity and yield were determined by means of gas chromatography. Substrates, batch sizes and analysis are compiled in Table 1.
99 %Chromat. With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran at 50℃; for 6 h; Schlenk technique In a 50 mE glass Schlenk tube, 14.2 mg (0.0200 mmol/Ru) of ruthenium complex D produced in Example 5 was added, and after replacement with nitrogen gas, 0.10 mE (0.10 mmol) of 1 M K093u (solution in THF), 1.8 mE of THF, and 137 mg (1.0 mmol) of a substrate were added, and then a balloon containing hydrogen gas was attached to the Schienk tube to conduct replacement with hydrogen gas, and stirred at 50° C. for 6 hours. After cooling, the reactant was analyzed by GC, and 3-pyridinemethanol was obtained with a GC yield of 99percent.
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3894 - 3897
[2] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1431 - 1440
[3] Dalton Transactions, 2012, vol. 41, # 34, p. 10136 - 10140,5
[4] Dalton Transactions, 2012, vol. 41, # 34, p. 10136 - 10140
[5] Inorganica Chimica Acta, 2019, vol. 486, p. 55 - 62
[6] Advanced Synthesis and Catalysis, 2016, vol. 358, # 5, p. 820 - 825
[7] Heterocycles, 1985, vol. 23, # 7, p. 1707 - 1722
[8] Chemical Communications, 2013, vol. 49, # 84, p. 9758 - 9760
[9] Organic Letters, 2018, vol. 20, # 9, p. 2654 - 2658
[10] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2785 - 2788
[11] Synthetic Communications, 1982, vol. 12, # 6, p. 463 - 468
[12] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 7, p. 1948 - 1953
[13] Patent: US2009/43102, 2009, A1, . Location in patent: Page/Page column 1-2
[14] Chemische Berichte, 1953, vol. 86, p. 1419,1422
[15] Patent: US2010/63294, 2010, A1, . Location in patent: Page/Page column 14
[16] European Journal of Organic Chemistry, 2013, # 11, p. 2061 - 2065
[17] Angewandte Chemie - International Edition, 2014, vol. 53, # 33, p. 8722 - 8726[18] Angew. Chem., 2014, vol. 126, # 33, p. 8867 - 8871,5
[19] Chemistry - A European Journal, 2015, vol. 21, # 30, p. 10851 - 10869
[20] Angewandte Chemie - International Edition, 2016, vol. 55, # 49, p. 15364 - 15368[21] Angew. Chem., 2016, # 128, p. 15590 - 15594,5
[22] Patent: US2017/44196, 2017, A1, . Location in patent: Paragraph 0350; 0351
[23] Chemistry - A European Journal, 2018, vol. 24, # 5, p. 1046 - 1052
[24] Organometallics, 2018, vol. 37, # 13, p. 2193 - 2201
  • 5
  • [ 500-22-1 ]
  • [ 6290-49-9 ]
  • [ 100-55-0 ]
  • [ 93-60-7 ]
  • [ 136138-66-4 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 28, p. 5269 - 5276
  • 6
  • [ 93-60-7 ]
  • [ 15031-77-3 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2381,2383
[2] Journal fuer Praktische Chemie (Leipzig), 1936, vol. &lt;2&gt; 146, p. 88,102
  • 7
  • [ 93-60-7 ]
  • [ 917-64-6 ]
  • [ 15031-77-3 ]
Reference: [1] Monatshefte fuer Chemie, 1931, vol. 57, p. 335[2] Chem. Zentralbl., 1926, vol. 97, # I, p. 3336
  • 8
  • [ 93-60-7 ]
  • [ 676-58-4 ]
  • [ 1885-14-9 ]
  • [ 33402-75-4 ]
  • [ 5470-70-2 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 151 - 157
[2] Heterocycles, 1984, vol. 22, # 1, p. 151 - 157
  • 9
  • [ 67-56-1 ]
  • [ 93-60-7 ]
  • [ 33402-75-4 ]
  • [ 5470-70-2 ]
  • [ 67367-26-4 ]
  • [ 26218-80-4 ]
Reference: [1] Chemistry Letters, 1980, p. 131 - 134
[2] Chemistry Letters, 1980, p. 131 - 134
[3] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1761 - 1766
  • 10
  • [ 93-60-7 ]
  • [ 107-92-6 ]
  • [ 1701-70-8 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 2285
  • 11
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  • [ 77-78-1 ]
  • [ 1690-72-8 ]
Reference: [1] Ann. Rep. Tanabe pharm. Res., 1958, vol. 3, p. 30,31[2] Chem.Abstr., 1959, p. 10214
  • 12
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  • [ 553-53-7 ]
YieldReaction ConditionsOperation in experiment
93.2% With hydrazine hydrate In ethanol at 20℃; for 3 h; Weigh the methyl 3-picolinate (2.74g, 20mmol)And anhydrous ethanol (15 mL) was added to a 50 mL round bottom flask,Stir at room temperature until the solid completely dissolves,Slowly dropping 30mmol of 80percent hydrazine hydrate,A large number of needle-like white solids appeared immediately,Continue stirring at room temperature for 3h, filter, rinse with a small amount of ethanol,Get 2.56g white needle crystals,Yield 93.2percent
75% With hydrazine hydrate In ethanol at 150℃; for 0.0833333 h; Microwave irradiation a. PREPARATION OF NICOTINOHYDRAZIDE [00473] To a solution of methyl nicotinate (0.73 mmol) in 0.3 mL of ethanol was added hydrazine hydrate (0.35 mL, 7.29 mmol). This reaction mixture was heated in a microwave reactor for 5 min at 150 °C. The reaction was allowed to cool to room temperature and diluted with 10 mL of MeOH, then concentrated. The residue was purified by column chromatography with MeOH/CH2Cl2 (1 :4) to afford 84 mg (75percent) of the desired product.
67% With hydrazine hydrate In methanol for 6.5 h; Reflux A mixture of nicotinic acid (3 g, 24 mmol), MeOH (60 mL) and H2SO4 (c) (12 mL) was heated at reflux for 1.5 h. The MeOH was distilled at reduced pressure and the residue was dissolved AcOEt (50 mL) and washed with saturated aqueous solution of NaHCO3 (3 .x. 10 mL). The organic phase was dried with anhydrous Na2SO4 and evaporated under reduced pressure. The residue, methyl nicotinate (white solid, 2.7 g, 83percent), was used in the next step without purification. A mixture of methyl nicotinate (2.7 g, 20 mmol), MeOH (4 mL) and NH2NH2*H2O (98percent, 0.95 mL) was heated at reflux for 6.5 h. The white solid, nicotinohydrazide, was filtered and washed several times with cold EtOH (1.8 g, 67percent).
67% With hydrazine hydrate In methanol at 20℃; for 12 h; Specific steps for synthesizing nicotinic acid hydrazide:4 g of methyl nicotinate and 25 mL of hydrazine hydrate were weighed and dissolved in 5 mL of anhydrous methanol. Stir at room temperature for 12 hours. Thin layerAfter the chromatographic reaction is completed, the solvent is removed by rotary distillation under reduced pressure.The residue was recrystallized from dry ethyl acetate to afford white crystal. The yield was 67percent.
67.3% With hydrazine hydrate In methanol at 20℃; Hydrazine hydrate (25mL) was added to a solution of 2 (4g, 9.2mmol) in methanol (5mL) at the room temperature. The solution was stirred overnight at room temperature. The solvent was evaporated and the crude product was recrystallized from ethanol to give the white solid 3. Yield: 2.69g (67.3percent). IR (KBr, v in cm−1): 3322, 3203, 3012, 2865, 1732, 1596, 1572, 1543, 1474, 1340, 952, 706. 1H NMR (400MHz, DMSO-d6): 10.05 (s, 1H), 9.05 (d, 1H, J=1.6Hz), 8.73 (dd, 1H, J1=1.6Hz, J2=4.8Hz), 8.22 (dt, 1H, J1=1.88Hz, J2=7.96Hz), 7.52 (dd, 1H, J1=4.84Hz, J2=7.9Hz), 4.68 (s, 2H). 13C NMR (100MHz, DMSO-d6): 164.91, 152.20, 148.58, 135.15, 129.35, 123.92 (Figs. S3, S4).

Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1381 - 1387
[2] Patent: CN104592217, 2018, B, . Location in patent: Paragraph 0032; 0033; 0034
[3] Patent: WO2017/11466, 2017, A1, . Location in patent: Paragraph 00473
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2158 - 2171
[5] Patent: CN108484582, 2018, A, . Location in patent: Paragraph 0031; 0036; 0037; 0038; 0039
[6] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2019, vol. 210, p. 105 - 110
[7] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 576 - 588
[8] Journal of the Chemical Society, 1953, p. 1358,1361
[9] Archiv der Pharmazie (Weinheim, Germany), 1951, vol. 284, p. 6
[10] Molecules, 2005, vol. 10, # 9, p. 1218 - 1228
[11] Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1785 - 1794
[12] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 683 - 689
[13] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2613 - 2616
[14] ChemMedChem, 2014, vol. 9, # 11, p. 2445 - 2448
[15] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9942 - 9959
[16] Patent: WO2016/162785, 2016, A1, . Location in patent: Page/Page column 21
[17] Chemical Biology and Drug Design, 2017, vol. 90, # 2, p. 200 - 209
[18] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 666 - 680
  • 13
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  • [ 446-26-4 ]
  • [ 1427-06-1 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
[2] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
  • 14
  • [ 93-60-7 ]
  • [ 78948-09-1 ]
  • [ 40134-18-7 ]
  • [ 135773-41-0 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 22, p. 6298 - 6301
  • 15
  • [ 646-06-0 ]
  • [ 93-60-7 ]
  • [ 5470-70-2 ]
  • [ 69971-44-4 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 21, p. 4162 - 4163
  • 16
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  • [ 676-58-4 ]
  • [ 1885-14-9 ]
  • [ 33402-75-4 ]
  • [ 5470-70-2 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 1, p. 151 - 157
[2] Heterocycles, 1984, vol. 22, # 1, p. 151 - 157
  • 17
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  • [ 93-60-7 ]
  • [ 33402-75-4 ]
  • [ 5470-70-2 ]
  • [ 67367-26-4 ]
  • [ 26218-80-4 ]
Reference: [1] Chemistry Letters, 1980, p. 131 - 134
[2] Chemistry Letters, 1980, p. 131 - 134
[3] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1761 - 1766
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  • [ 33402-75-4 ]
  • [ 5470-70-2 ]
  • [ 67367-26-4 ]
  • [ 26218-80-4 ]
Reference: [1] Chemistry Letters, 1980, p. 131 - 134
[2] Chemistry Letters, 1980, p. 131 - 134
[3] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1761 - 1766
  • 19
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Reference: [1] Journal of Molecular Structure, 2005, vol. 743, # 1-3, p. 1 - 6
  • 20
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  • [ 35779-35-2 ]
Reference: [1] Heteroatom Chemistry, 2012, vol. 23, # 1, p. 66 - 73
  • 21
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  • [ 75358-89-3 ]
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  • [ 89809-65-4 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 22
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  • [ 75358-89-3 ]
Reference: [1] Patent: WO2015/81891, 2015, A1,
  • 23
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  • [ 141-43-5 ]
  • [ 6265-73-2 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 7, p. 605 - 614
[2] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 8, p. 1579 - 1589
[3] Chemische Berichte, 1954, vol. 87, p. 1632
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 200,203
[5] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 5, p. 1041 - 1058
[6] Patent: WO2007/38772, 2007, A1, . Location in patent: Example 2; 3
  • 24
  • [ 93-60-7 ]
  • [ 100-51-6 ]
  • [ 94-44-0 ]
YieldReaction ConditionsOperation in experiment
99% at 110℃; for 6 h; Molecular sieve General procedure: Lanthanum nitrate hexahydrate (La (NO 3) 3 .6H 2 0, 17.3 mg, 0.04 mmol) and nitrous oxide were added to a Soxhlet reflux vessel containing absorbent cotton and 2.0 g of dried pelletized molecular sieves 5 A (MS 5 A) , Tri-n-octylphosphine (90percent purity, 40 μL, 0.08 mmol) and dimethyl carbonate dehydrated by distillation (8 mL) were placed and stirred at room temperature for 1 to 2 minutes. The resulting mixture was heated under heating reflux conditions (bath temperature of 110 ° C.) for 1 hour. The mixed solution was cooled to room temperature, the solvent component was distilled off under reduced pressure, and the mixture was dried at room temperature under 5 Torr or less for 1 hour to prepare a catalyst. In the reaction vessel, n-hexane (8 mL) as a solvent, 4-nitrobenzoic acid ester (4.0 mmol) as a carboxylic acid ester and benzyl alcohol (4.0 mmol) as a primary alcohol were added in this order. Immediately, the reactor was heated to reflux condition (bath temperature: 90 ° C.). Refluxing was continued while appropriately checking the progress of the reaction by TLC, and after 5 hours, the completion of the reaction was confirmed by TLC. Thereafter, the reaction mixture was cooled to room temperature, a small amount of water (0.3 to 0.5 mL) was added, and the reaction was stopped by stirring at room temperature for 5 minutes. The reaction mixture was dried over magnesium sulfate, filtered, and the filtrate was concentrated. The product was isolated from the concentrate by silica gel column chromatography (n-hexane: ethyl acetate). The yield was 99percent.In Examples 25 to 29 and Comparative Examples 10 to 14, a product was obtained in the same manner as in Example 24, except that the compound shown in Table 4 was used as the carboxylic acid ester and the reaction time was changed. In addition, in Example 30 and Comparative Example 15, production was carried out in the same manner as in Example 24, except that methyl benzoate was used as the carboxylic acid ester, cyclohexanol as the secondary alcohol was used as the alcohol compound, and the reaction time was changed I got things. However, in Examples 26, 27 and 29 and Comparative Examples 11, 12 and 15, as shown in Table 4, the amounts of lanthanum compounds and ligands used were increased. The results are shown in Table 4 including the results of Example 24 and Comparative Example 9.
Reference: [1] Patent: JP5804472, 2015, B2, . Location in patent: Paragraph 0054; 0055; 0056
[2] Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2812 - 2819
[3] Chemical Communications, 2012, vol. 48, # 76, p. 9465 - 9467
[4] European Journal of Organic Chemistry, 2013, # 2, p. 326 - 331
[5] Organic Letters, 2008, vol. 10, # 11, p. 2187 - 2190
  • 25
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  • [ 17955-46-3 ]
  • [ 59020-10-9 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 2, p. 385 - 388
  • 26
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  • [ 75-05-8 ]
  • [ 30510-18-0 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With sodium hydride In toluene at 0℃; for 0.5 h;
Stage #2: for 72 h; Reflux
To a stirred solution of methyl nicotinate (XVIII; 8 g; 58 mmol) in toluene (110 mL) was added sodium hydride (2.8 g; 110 mmol) at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and then acetonitrile (12 g; 91 mmol) was added. The reaction mixture was heated to a reflux for 72 hours. The reaction mixture was cooled, concentrated at reduced pressure and diluted with ice cold water. The reaction mixture was acidified using glacial acetic acid. Theaqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over Na2504, filtered and concentrated under vacuum to afford 3-oxo-3-(pyridin-3-yl)propanenitrile as a yellow solid (XIX; 6 g, 70percent yield). MS (M-1):145.01.
Reference: [1] Patent: WO2015/97122, 2015, A1, . Location in patent: Page/Page column 81; 82
[2] Patent: WO2012/129258, 2012, A1, . Location in patent: Page/Page column 150; 151
  • 27
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  • [ 446-26-4 ]
  • [ 1427-06-1 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
[2] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
  • 28
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  • [ 622-47-9 ]
  • [ 40061-21-0 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 3, p. 580 - 585
  • 29
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  • [ 25015-63-8 ]
  • [ 1345455-94-8 ]
  • [ 1195-66-0 ]
Reference: [1] Organometallics, 2011, vol. 30, # 21, p. 5556 - 5559
  • 30
  • [ 93-60-7 ]
  • [ 25015-63-8 ]
  • [ 1195-66-0 ]
Reference: [1] Organometallics, 2011, vol. 30, # 21, p. 5556 - 5559
  • 31
  • [ 93-60-7 ]
  • [ 78-90-0 ]
  • [ 79455-30-4 ]
  • [ 210362-58-6 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 5, p. 429 - 435
  • 32
  • [ 93-60-7 ]
  • [ 65973-52-6 ]
YieldReaction ConditionsOperation in experiment
83% for 7 h; Heating / reflux PREPARATION. 84 4,6-Dichloro-nicotinic acid methyl ester 3-Pyridinecarboxylic acid [(27g, 160mmol), J.Het. Chem, 20, 1363; 1983] was added portionwise to phosphorus oxychloride (180mL) and the mixture was . heated under reflux for 7 hours and-stirred at room temperature for 18-HOURS. The mixture was then-concentrated in-vacuo to a low volume and. the residue was quenched with water The aqueous mixture was NEUTRALISED WITH SODIUM hydrogen carbonate solution and extracted with chloroform (3x150mL). The combined organic solutions were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a red oil in 83percent yield, 27.2g, 1HNMR (CDCL3, 400MHZ) No.: 3.96(S, 3H), 7.47(S, 1H), 8.85(S,1H), MS APCI+ M/Z 206 [MH]+
Reference: [1] Patent: WO2005/28452, 2005, A1, . Location in patent: Page/Page column 95
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