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Chemical Structure| 89-00-9
Chemical Structure| 89-00-9
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Product Details of [ 89-00-9 ]

CAS No. :89-00-9 MDL No. :
Formula : C7H5NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :GJAWHXHKYYXBSV-UHFFFAOYSA-N
M.W : 167.12 Pubchem ID :1066
Synonyms :
NSC 13127;NSC 403247;NSC 18836

Calculated chemistry of [ 89-00-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.16
TPSA : 87.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.26
Log Po/w (XLOGP3) : 0.24
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -1.47
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : -0.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.27
Solubility : 9.07 mg/ml ; 0.0543 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.85 mg/ml ; 0.023 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.77
Solubility : 28.7 mg/ml ; 0.172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 89-00-9 ]

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 [ 89-00-9 ]

* 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 [ 89-00-9 ]
  • Downstream synthetic route of [ 89-00-9 ]

[ 89-00-9 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 89-00-9 ]
  • [ 1462-86-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
  • 2
  • [ 89-00-9 ]
  • [ 498-95-3 ]
Reference: [1] Chemische Berichte, 1895, vol. 28, p. 3153
  • 3
  • [ 89-00-9 ]
  • [ 13472-80-5 ]
Reference: [1] Chemische Berichte, 1887, vol. 20, p. 1351
  • 4
  • [ 89-00-9 ]
  • [ 108-24-7 ]
  • [ 4733-69-1 ]
  • [ 5657-51-2 ]
Reference: [1] Helvetica Chimica Acta, 1958, vol. 41, p. 498,509
  • 5
  • [ 89-00-9 ]
  • [ 4664-00-0 ]
YieldReaction ConditionsOperation in experiment
84% at 140℃; for 6 h; To 1000 ml three-necked flask were added 167 g of 2,3-pyridinedicarboxylic acid (1.0 mol) and 300 ml of concentrated aqueous ammonia (28percent), followed by stirring under reflux for 6 hours at 140 °C, the liquid reaction mixture became dark brown, thin layer Analysis of the reaction was followed, when the starting material 2,3-pyridinedicarboxylic acid completion of the reaction, the reaction mixture was cooled to room temperature, under stirring, the reaction mixture was cooled as slowly pouredinto 500 ml of cold water, a large number of gray solid immediately precipitated, was filtered and the filter cake washed with coldwater and dried in vacuo overnight at 60 °C, to give a gray powder 125 g, yield 84percent.
47% at 100 - 120℃; for 2.5 h; Reflux Pyridine-2,3-dicarboxylic acid (8.40 g, 50.30 mmol, 1 eq) was suspended in acetic anhydride (11.0 mL, 116.50 mmol, 2.3 eq) and the mixture was heated at 120 °C, distilling 9.5 mL of acetic acid.
After cooling at 100 °C the acetamide (6.70 g, 113.60 mmol, 2.2 eq) was added portionwise in 5 min.
The reaction was then heated at reflux for 2.5 h.
After cooling at room temperature, the precipitate was filtered off and washed with water (2 * 12 mL) to give the desired product as grey solid after crystallization with EtOH/H2O 95:5 (3.46 g, 47percent). Mp. 230-231 °C. 1H NMR (300 MHz, DMSO-d6) δ 11.63 (br s, NH), 8.93 (d, J = 4.9 Hz, 1-H), 8.22 (d, J = 7.7 Hz, 1-H), 7.74 (dd, J = 7.6/4.9 Hz, 1-H). IR (KBr) 3483, 3189, 3100, 1735, 1704 cm-1.
Reference: [1] Patent: CN102746294, 2016, B, . Location in patent: Paragraph 0077; 0078
[2] Heterocycles, 2002, vol. 57, # 10, p. 1881 - 1890
[3] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[4] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 58 - 66,9
[5] Molecules, 2000, vol. 5, # 3, p. 481 - 482
[6] Patent: US5801183, 1998, A,
[7] Chemical Communications, 2016, vol. 52, # 38, p. 6471 - 6474
[8] Patent: CN106083846, 2016, A, . Location in patent: Paragraph 0013; 0014; 0015
  • 6
  • [ 699-98-9 ]
  • [ 89-00-9 ]
  • [ 4664-00-0 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: Reflux
The 8.351g (50mmol) 2,3- pyridinedicarboxylic acid (Compound -1), and 10.209g of acetic anhydride in a reactor, under stirring, to the reactor was added 7.383g (125mmol) acetamide, heating to reflux, TLC the reaction to the raw material tracking point disappears, cooling, gray crystals precipitated solid was suction filtered and washed with cold water, to give 5H- pyrrolo [3,4-b] pyridine -5,7 (6H) - dione (compound -1), a yield of 66percent.
Reference: [1] Patent: CN105541833, 2016, A, . Location in patent: Paragraph 0149; 0150; 0151
  • 7
  • [ 89-00-9 ]
  • [ 57-13-6 ]
  • [ 4664-00-0 ]
Reference: [1] Journal of the Indian Chemical Society, 1933, vol. 10, p. 111,114
[2] Patent: CN106188047, 2016, A, . Location in patent: Paragraph 0016
  • 8
  • [ 89-00-9 ]
  • [ 108-24-7 ]
  • [ 4664-00-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021
  • 9
  • [ 89-00-9 ]
  • [ 699-98-9 ]
YieldReaction ConditionsOperation in experiment
91% With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3 h; Inert atmosphere; Reflux General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. .
72.1% at 20 - 110℃; in room temperature,A mixture of 250 mL of acetic anhydrideAdded to1000ml of three bottles,100.0 g (0.598 mol l.Oeq) of 2,3-pyridinedicarboxylic acid was added,After finishing,Start heating to 110 ° C to reflux,After stirring for 2-3 hours,The reaction is complete,Cooled to room temperature,Add 500ml of carbon tetrachloride to precipitate a large amount of white solid,filter,The filter cake was rinsed with 100 mL of carbon tetrachloride,To give 64.0 g of the first product acid anhydride (yield 72.1percent),Do not need to go directly to the next step.
1.55 g at 115℃; for 4 h; A mixture of pyridine-2,3-dicarboxylic acid (2 g, 12 mmol) and acetic anhydride was heated at 115° C. for 4 h.
Excess reagent was removed under reduced pressure.
The remaining solid was triturated with hot carbon tetrachloride.
After cooling, the solid was collected by vacuum filtration and dried overnight under vacuum at 60° C. to give furo[3,4-b]pyridine-5,7-dione (1.55 g, 10.4 mmol).
1H NMR (400 MHz, DMSO-d6) δ 9.10 (dd, J=4.9, 1.5 Hz, 1H), 8.50 (dd, J=7.8, 1.5 Hz, 1H), 7.90 (dd, J=7.8, 4.9 Hz, 1H).
Reference: [1] Chinese Journal of Chemistry, 2015, vol. 33, # 11, p. 1269 - 1275
[2] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3160 - 3163
[3] Journal of Organic Chemistry, 1989, vol. 54, # 14, p. 3264 - 3269
[4] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
[5] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1565 - 1570
[6] Tetrahedron, 2001, vol. 57, # 44, p. 9101 - 9108
[7] Patent: CN103864696, 2016, B, . Location in patent: Paragraph 0029-0032
[8] Justus Liebigs Annalen der Chemie, 1895, vol. 288, p. 257
[9] Chemische Berichte, 1887, vol. 20, p. 1209
[10] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 328
[11] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1632
[12] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1632
[13] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1632
[14] Journal of Organic Chemistry, 1961, vol. 26, p. 808 - 811
[15] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 6, p. 1757 - 1763
[16] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1834 - 1840
[17] Heterocyclic Communications, 2001, vol. 7, # 5, p. 439 - 444
[18] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 3, p. 306 - 309
[19] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 12, p. 1446 - 1451
[20] Patent: WO2009/125425, 2009, A2, . Location in patent: Page/Page column 6; 9
[21] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61
[22] Patent: US2015/65510, 2015, A1, . Location in patent: Paragraph 0099; 0100
[23] Synthetic Communications, 2017, vol. 47, # 3, p. 238 - 244
  • 10
  • [ 89-00-9 ]
  • [ 89-01-0 ]
  • [ 699-98-9 ]
Reference: [1] Patent: EP639183, 1998, B1,
  • 11
  • [ 89-00-9 ]
  • [ 108-24-7 ]
  • [ 699-98-9 ]
Reference: [1] Journal of the American Chemical Society, 1915, vol. 37, p. 1949
[2] Justus Liebigs Annalen der Chemie, 1895, vol. 288, p. 257
[3] Chemische Berichte, 1887, vol. 20, p. 1209
  • 12
  • [ 89-00-9 ]
  • [ 10026-13-8 ]
  • [ 699-98-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 328
  • 13
  • [ 67-56-1 ]
  • [ 89-00-9 ]
  • [ 24195-07-1 ]
  • [ 605-38-9 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 3, p. 205 - 232
  • 14
  • [ 67-56-1 ]
  • [ 89-00-9 ]
  • [ 605-38-9 ]
YieldReaction ConditionsOperation in experiment
95.8%
Stage #1: at 20℃; for 0.5 h;
Stage #2: at 60℃;
The compound of formula I (80g, 0.48mol) was dissolved in methanol (400ml), and stirred at rt for 30min, then a solution of concentrated sulfuric acid (94.1g, 0.96mol), the completion of the dropwise addition of about half an hour, heated to 60 , the reaction overnight.Spin dry methanol under reduced pressure, and the concentrate was slowly poured into aqueous sodium carbonate solution, there are a lot of gas evolution.PH was adjusted to 7-8, (1000ml * 2) and extracted with methylene chloride, dried over anhydrous sodium sulfate, and dried under reduced pressure to spin, to give a pale yellow solid was 89.7g, 99percent purity, yield 95.8percent.
85.63% at 60℃; for 10 h; Concentrated sulfuric acid (17.61 g, 179.51 mmol, 9.57 mL, 1.50 eq) was added to a solution of pyridine-2,3-dicarboxylic acid (20.00 g, 119.67 mmol, 1.00 eq) in methanol (150.00 mL).
The mixture was stirred at 60 °C for 10 hours.
A sodium carbonate solution was added to adjust the pH to about 9 and the mixture was extracted with ethyl acetate (200 mL * 2).
The combined organic layers were concentrated under reduced pressure and the residue was chromatographed on silica gel (SiO2, petroleum ether / ethyl acetate = 20/1 to 3: 1) to deliver dimethyl pyridine-2,3-dicarboxylate (20.00 g, 102.47 mmol, 85.63percent yield) as a white solid.
75% for 16 h; Reflux Quinolinic acid (5, 15.6 g, 94.0 mmol, 1.00 eq.) was dissolved in MeOH (100 ml) and concentrated H2SO4 (10 ml) was added dropwise. The reaction mixture was heated to reflux for 16 h H2O (80 ml) was added and the mixture was adjusted to pH 8 by addition of NaOH platelets and extracted with CH2Cl2 (3 * 100 ml). The combined organic layers were dried (anhydr. Na2SO4) and the solvent was removed in vacuo. Yellow solid, yield 13.8 g (75percent). C9H9NO4 (195.2 g/mol). Mp = 55 °C. 1H NMR (600 MHz, CD3OD): δ = 3.96 (s, 3H, CH3), 3.99 (s, 3H, CH3), 7.70 (dd, J = 8.0, 4.9 Hz, 1H, 5-H), 8.35 (dd, J = 8.0, 1.6 Hz, 1H, 4-H), 8.78 (dd, J = 4.9, 1.6 Hz, 1H, 6-H). 13C NMR (151 MHz, CD3OD): δ = 55.1 (1C, CO2CH3), 55.5 (1C, CO2CH3), 126.7 (1C, 5-C), 127.5 (1C, 4-C), 139.4 (1C, 3-C), 152.0 (1C, 6-C), 152.9 (1C, 2-C), 168.2 (1C, C=O), 166.9 (1C, C=O). Exact MS (APCI): m/z = 196.0609 (calcd. 196.0604 for C9H10NO4+ [M + H+]).
54% Heating / reflux To the solution of pyridine-2,3-dicarboxylic acid (50 g, 300 mmol) in MeOH (300 mL) was added SOCl2 (44 mL, 600 mmol), and the mixture was refluxed overnight. Volatiles were removed under vacuum, sat. Na2CO3 was added, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum to give dimethyl pyridine-2,3-dicarboxylate as a colorless oil. Yield 32 g, 54percent.
45.7 g for 24 h; Reflux To a solution of pyridine-2,3-dicarboxylic acid (50.0 g, 0.299 mol) in methanol (500 ml) was added con. sulfuric acid (20 ml). After heated to reflux for 24 hours, the mixture wasbasified with saturate sodium carbonate solution until pH=8 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated to give D78 (45.7 g) as a white solid. 1H NMR (ODd3) 6 ppm = 3.95 (s, 3H), 4.01 (s, 3H), 7.51 (m, 1H), 8.18 (dd, J = 6.4, 1.6Hz, 1 H), 8.77 (dd, J = 6.8, 2.0 Hz, 1 H).
45.7 g for 24 h; Reflux To a solution of pyridine-2,3-dicarboxylic acid (50.0 g, 0.299 mol) in methanol (500 ml) was added con. sulfuric acid (20 ml). After heated to reflux for 24 hours, the mixture was basified with saturate sodium carbonate solution until pH=8 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated to give D78 (45.7 g) as a white solid. 1H NMR (CDCl3) δ ppm=3.95 (s, 3H), 4.01 (s, 3H), 7.51 (m, 1H), 8.18 (dd, J=6.4, 1.6 Hz, 1H), 8.77 (dd, J=6.8, 2.0 Hz, 1H).

Reference: [1] Patent: CN105566319, 2016, A, . Location in patent: Paragraph 0185; 0186; 0187; 0188
[2] Australian Journal of Chemistry, 1984, vol. 37, # 1, p. 87 - 94
[3] Patent: EP3252059, 2017, A1, . Location in patent: Paragraph 0686; 0686-0688
[4] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 397 - 404
[5] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 433 - 450
[6] Organic Process Research and Development, 2012, vol. 16, # 11, p. 1854 - 1860
[7] Patent: WO2008/108988, 2008, A1, . Location in patent: Page/Page column 60
[8] Chemische Berichte, 1894, vol. 27, p. 1788
[9] Russian Journal of General Chemistry, 1999, vol. 69, # 11, p. 1823 - 1826
[10] Journal of the American Chemical Society, 2003, vol. 125, # 1, p. 296 - 304
[11] Patent: WO2013/92893, 2013, A1, . Location in patent: Page/Page column 48; 49
[12] Patent: US2014/357653, 2014, A1, . Location in patent: Paragraph 0310; 0311; 0312
  • 15
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  • [ 605-38-9 ]
Reference: [1] Patent: US5770597, 1998, A,
[2] Patent: WO2010/100215, 2010, A1, . Location in patent: Page/Page column 27-28
  • 16
  • [ 89-00-9 ]
  • [ 144-55-8 ]
  • [ 605-38-9 ]
Reference: [1] Patent: US5194430, 1993, A,
  • 17
  • [ 186581-53-3 ]
  • [ 89-00-9 ]
  • [ 605-38-9 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 2080
  • 18
  • [ 67-56-1 ]
  • [ 89-00-9 ]
  • [ 24195-07-1 ]
  • [ 605-38-9 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 3, p. 205 - 232
  • 19
  • [ 89-00-9 ]
  • [ 64-17-5 ]
  • [ 2050-22-8 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: for 72 h; Heating / reflux
Stage #2: With ammonia; ammonium chloride In water
To a suspension of 2,3-pyridinedicarboxylic acid (200 g, 1.2 mol) in ethanol (800 ml) was added cone H2SO4 (100 ml) and this mixture was heated to reflux for 3 days (mechanical stirring). It was then cooled down to r.t. and added to crushed ice. Cone NH4OH (405 ml) was then added slowly and the pH was adjusted to 9 by addition of some aq. NH4Cl. The products were extracted into i-PrOAc, dried over Na2SO4 and concentrated to yield 182.48 g of an orange oil containing 88percent of the diester (60percent yield), 8.1percent of ethyl 3-pyridinecarboxylate and 3.5percent i-PrOAc. This mixture was used as such in the next step.
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[2] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6863 - 6866
[3] Journal of the Indian Chemical Society, 1994, vol. 71, # 2, p. 75 - 80
[4] Patent: WO2006/122403, 2006, A1, . Location in patent: Page/Page column 31-32
[5] Chemische Berichte, 1894, vol. 27, p. 1788
  • 20
  • [ 89-00-9 ]
  • [ 2050-22-8 ]
Reference: [1] Patent: EP566567, 1997, B1,
  • 21
  • [ 89-00-9 ]
  • [ 2050-22-8 ]
Reference: [1] Journal of Molecular Structure, 2012, vol. 1018, p. 21 - 27
[2] Patent: US2015/65510, 2015, A1,
  • 22
  • [ 89-00-9 ]
  • [ 36052-27-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
  • 23
  • [ 89-00-9 ]
  • [ 40107-93-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 58 - 66,9
[2] Chemical Communications, 2016, vol. 52, # 38, p. 6471 - 6474
[3] Patent: CN105541833, 2016, A,
  • 24
  • [ 89-00-9 ]
  • [ 100-46-9 ]
  • [ 18184-75-3 ]
YieldReaction ConditionsOperation in experiment
91% With silica gel In neat (no solvent) at 150℃; for 18 h; Inert atmosphere; Sealed tube General procedure: These compounds were prepared using the same procedure as reported above, but at 150°C for 18–26h. Following work up, the crude products were purified on 15cm×2.5cm silica gel columns eluted with 60–80percent EtOAc in hexanes. The isolated yields are given in Table 3. Note: Saturated NH4Cl was used for washing the pyridine derivatives instead of 1M HCl.
90% With acetic anhydride In toluene at 30 - 60℃; In a flask 120g2,3- pyridinedicarboxylic acid, 110g of acetic anhydride, heated up with stirring, the solid is gradually dissolved, and when the internal temperature reached 92 deg.] C, all the solid had dissolved, 92 ~ 95 temperature control for 2 to 3 hours to 2, 3-pyridyl acid ≤0.1percent, the reaction was completed, cooling to 50 ~ 60 , evaporated under reduced pressure, heated to 80 ~ 85 , no flow to continue evaporated under reduced pressure, cooling to 50 ~ 60 , toluene was added 40g , mixing temperature, the toluene was evaporated to dryness under reduced pressure, 40g of toluene and then once with the above-described method, steaming complete, 169g of toluene was added, heated to 40 ~ 50 stir, cooled to 30 ~ 40 benzylamine was slowly added dropwise 92.3g dropping process control temperature does not exceed 55 ,2 hours drop end, at a temperature of 40 ~ 50 for 3 to 4 hours to pyridine-2,3-dicarboxylic acid anhydride ≤0.1percent, the reaction was completed, water bath heating, external temperature control 85 evaporated to dryness under reduced pressure, the residue was added 110g acetic anhydride, heated up with stirring, the temperature control 92 ~ 95 for 1 to 2 hours to precipitate solid, and stirring was continued for 1 to 2 hours to ring-opened product ≤0.1percent, the reaction was completed, cooling to 50 ~ 60 distilled off under reduced pressure dry, warmed to 80 ~ 85 , no flow to continue distilled off under reduced pressure, temperature lowered to room temperature, was added 200mL95percent ethanol, cooled to 0 stirred for 5 hours, filtered, cooled to 5 cake was washed with 95percent ethanol and washed 28mLx3 three times, drained, dried in vacuo to give an off-white solid 6-benzyl-pyrrolo [3,4-b] pyridine-5,7-dione 150g, yield 88 ~ 90percent
Reference: [1] Tetrahedron, 2015, vol. 71, # 48, p. 9101 - 9111
[2] Patent: CN105777750, 2016, A, . Location in patent: Paragraph 0024; 0025; 0040
[3] Asian Journal of Chemistry, 2013, vol. 25, # 15, p. 8701 - 8707
  • 25
  • [ 89-00-9 ]
  • [ 100-46-9 ]
  • [ 18184-75-3 ]
Reference: [1] Patent: US5654318, 1997, A,
  • 26
  • [ 89-00-9 ]
  • [ 18184-75-3 ]
Reference: [1] Heterocycles, 2002, vol. 57, # 10, p. 1881 - 1890
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 6, p. 1757 - 1763
[3] South African Journal of Chemistry, 2012, vol. 65, p. 53 - 61
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1013 - 1021
[5] Chinese Journal of Chemistry, 2015, vol. 33, # 11, p. 1269 - 1275
[6] Synthetic Communications, 2017, vol. 47, # 3, p. 238 - 244
[7] Patent: CN102746294, 2016, B,
  • 27
  • [ 89-00-9 ]
  • [ 115012-09-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 58 - 66,9
  • 28
  • [ 89-00-9 ]
  • [ 115012-09-4 ]
  • [ 115012-10-7 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 38, p. 6471 - 6474
[2] Patent: CN105541833, 2016, A,
  • 29
  • [ 67-56-1 ]
  • [ 89-00-9 ]
  • [ 588702-69-6 ]
Reference: [1] Patent: WO2005/63710, 2005, A1, . Location in patent: Page/Page column 34
  • 30
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  • [ 5654-94-4 ]
Reference: [1] Patent: CN102746294, 2016, B,
[2] Patent: CN102746294, 2016, B,
[3] Patent: CN102746294, 2016, B,
[4] Patent: CN102746294, 2016, B,
[5] Patent: CN102746294, 2016, B,
[6] Patent: CN102746294, 2016, B,
  • 31
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  • [ 89-00-9 ]
  • [ 521980-82-5 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: for 48 h; Reflux
Stage #2: at 40 - 55℃; for 50 h;
To a suspension of pyridine-2,3-dicarboxylic acid (50 g, 300 mmol) in MeOH (500 mL) was added concentrated H2SO4 (10 mL) slowly. The mixture was heated at reflux for 48 h, then cooled to 40 °C, followed by the dropwise addition of Br2 (38 mL, 750 mmol) over 2 h. The reaction was heated at 55 °C for 48 h, and then concentrated in vacuo. The residue was dissolved in isopropyl acetate (500 mL), and the resulted solution was washed with saturated aqueous a2S203 (200 mL x 4), followed by brine (400 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow solid (52 g, 63percent). MS (ESI, pos. ion) m/z: 274.0 [M + H]+; FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) δ (ppm): 8.75-8.76 (d, J= 2.2 Hz, 1H), 8.23-8.24 (d, J= 2.2 Hz, 1H), 3.93 (s, 1H), 3.89 (s, 1H).
63%
Stage #1: for 48 h; Reflux
Stage #2: at 40 - 55℃; for 50 h;
A solution of pyridyl 2,3-dicarboxylic acid (50 g, 300 mmol)Suspended in methanol (500 mL)To this was slowly added concentrated sulfuric acid (10 mL).After the mixture was refluxed for 48 hours,Cooled to 40 ° C, within 2 hours,To this was added bromine (38 mL, 750 mmol).The reaction solution was stirred at 55 ° C for 48 hours,Concentrated under reduced pressure.The residue was dissolved in isopropyl acetate (500 mL) and the resulting solution was obtainedThe residue was washed with sodium thiosulfate saturated solution (200 mL x 4), brine (400 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 5/1) to give the title compound as a yellow solid (52 g, 63percent)
Reference: [1] Patent: WO2014/89324, 2014, A1, . Location in patent: Paragraph 0284
[2] Patent: CN104016979, 2017, B, . Location in patent: Paragraph 0800; 0801; 0802; 0803
[3] Patent: US2012/122899, 2012, A1, . Location in patent: Page/Page column 18
[4] Patent: WO2012/129013, 2012, A1, . Location in patent: Page/Page column 29-30
[5] Patent: WO2013/169563, 2013, A1, . Location in patent: Page/Page column 69; 70
[6] Patent: WO2013/169574, 2013, A2, . Location in patent: Page/Page column 65; 66
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Chemical Structure| 138946-42-6

A1268542[ 138946-42-6 ]

2,3-Pyridinedicarboxylic Acid-d3

Reason: Stable Isotope