[ CAS No. 699-98-9 ]

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2D
Chemical Structure| 699-98-9
Chemical Structure| 699-98-9
Structure of 699-98-9

Quality Control of [ 699-98-9 ]

Purity: {[proInfo.showProBatch.pb_purity]}

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Product Details of [ 699-98-9 ]

CAS No. :699-98-9MDL No. :MFCD00005915
Formula :C7H3NO3Boiling Point :334.6°C at 760 mmHg
Linear Structure Formula :C5H3NC2O3InChI Key :-
M.W :149.10Pubchem ID :-
Synonyms :

Computed Properties of [ 699-98-9 ]

TPSA : 56.3 H-Bond Acceptor Count : 4
XLogP3 : 0.6 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 699-98-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 699-98-9 ]

  • Upstream synthesis route of [ 699-98-9 ]

[ 699-98-9 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
91% With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3.00 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 4.00 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
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Reference: [1] Patent: EP639183, 1998, B1
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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
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 328
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