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[ CAS No. 533-37-9 ]

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Chemical Structure| 533-37-9
Chemical Structure| 533-37-9
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CAS No. :533-37-9 MDL No. :MFCD00005933
Formula : C8H9N Boiling Point : 212.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :119.16 g/mol Pubchem ID :68292
Synonyms :

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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:

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  • Upstream synthesis route of [ 533-37-9 ]
  • Downstream synthetic route of [ 533-37-9 ]

[ 533-37-9 ] Synthesis Path-Upstream   1~7

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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1984, # 5, p. 265 - 266
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1984, # 5, p. 265 - 266
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  • [ 41598-71-4 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 9, p. 1879 - 1882
[2] Synlett, 2013, vol. 24, # 7, p. 837 - 838
[3] RSC Advances, 2015, vol. 5, # 126, p. 104509 - 104515
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 12, p. 2208 - 2212
[2] Chemische Berichte, 1991, vol. 124, # 3, p. 571 - 576
[3] Synlett, 2013, vol. 24, # 7, p. 837 - 838
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  • [ 28566-14-5 ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; manganese(II) triflate In water at 20℃; for 24 h; A solution of 0.883 mg of Mn (OTf) 2 (0.5 molpercent), 60 mg of 2,3-cyclopentenopyridine, 0.35 g of 65percent aqueous TBHP and 2.5 ml of water was added successively to a 25 mL round bottom flask, in the air at room temperature for 24 hours, the reaction solution was extracted with 3 x 5 mL of ethyl acetate, the ethyl acetate layer was collected, dried over anhydrous sodium sulfate, filtered and the ethyl acetate was distilled off, using petroleum ether and ethyl acetate in a volume ratio of 5: 1 as eluent, the product of 6,7-dihydro-5H-cyclopenta [b] pyridin-5-one 60.5 mg was obtained as a pale yellow solid in a yield of 91percent by silica gel column chromatography.
63% With tert.-butylhydroperoxide In water at 60℃; for 12 h; General procedure: A 15‐mL RBF was charged with substrate (0.5 mmol),MnOx‐N(at)C catalyst (1 mg, pyrolysis at 600 °C) and TBHP (1.5mmol, 65percent in H2O). The flask was then sealed, and the mixturewas heated at 60 °C for 12 h. The reaction was cooled to roomtemperature and diluted with ethyl acetate (4 mL), before beingcentrifuged at 10000 r/min for 1 min to separate the catalyst.The supernatant was removed and the catalyst waswashed with ethyl acetate (5 × 4 mL). The supernatant wassubsequently combined the ethyl acetate wash solutions andevaporated to dryness to give a residue, which was purified byflash column chromatography over silica gel (ethyl acetate/n‐hexane = 1:10, v/v).
35% With chromium(VI) oxide; sulfuric acid; acetic acid In water at 10℃; To a stirring solution of 6,7-dihydro-5H-cyclopenta[b]pyridine SM1 (3.83 g, 32 mmol) in HOAc (20 mL) and conc.H2S04 (3.5 ml) was added a solution of Cr03 (6.7 g, 67.2mmol) in 10 mlof HOAc and 2 mL of H20. The temperature was kept below 10 °C during the addition. Afteraddition completed the resultant mixture was stirred at room temperature overnight. The mixture was then poured into crushed ice and treated with NH4OH to pH 11 and extracted with DCM. The organic phase was worked up and purified by silica gel column chromatography eluting with 50percent EtOAc/Hexane to afford compound 1(1.1 g, 35percent). LC-MS: m/z = 134.0[M+H]
18.6%
Stage #1: With chromium(VI) oxide; sulfuric acid; acetic acid In water at 0℃;
Stage #2: With ammonia In water at 0℃;
6,7-Dihydro-[1]pyrindin-5-onexxxi: To a solution of 6,7-dihydro-5H-[1]pyrindine (11.00 g, 92.30 mmol) in 50 mL HOAc and 10 mL H2SO4 at 0° C. was added CrO3 (18.50 g, 0.19 mol) dissolved in 6 mL H2O and 30 mL HOAc. The resulting mixture was stirred overnight, cooled on ice and basified with NH4OH to pH 11. The mixture was extracted with CHCl3 (3.x.250 mL), and the combined organic extracts were washed with H2O (3.x.100 mL), brine (1.x.200 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (2:3) as the eluant gave 2.29 g (18.6percent) of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 2.77-2.83 (m, 2H), 3.27-3.33 (m, 2H), 7.34 (dd, J=7.62 Hz, 1H), 8.03 (dd, J=7.62 Hz, 1H), 8.82 (dd, J=4.69 Hz, 1H).
5 g at 15 - 25℃; Step A 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one (24a)
To a solution of 6,7-dihydro-5H-cyclopenta[b]pyridine (10 g, 83.99 mmol)[comercially available from Sigma-Aldrich, St. Louis, MO, USA] in a mixture of acetic acid and sulfuric acid (5: 1, 60 mL), was added CrO3(16.7 g, 167.1 mmol) dissolved in acetic acid (30 mL). The reaction mixture was stirred overnight at room temperature. The reaction mixture was cooled to 0°C and the pH was adjusted to ~ (approximately) 11 using ammonium hydroxide and then extracted with dichloro-methane. The combined organic layers were washed with water and brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the crude mass was purified by column chromatography using 50percent ethyl acetate in petroleum ether (v/v) to afford 24a (5 g). Molecular Formula: C8H7NO; LC-MS purity: 94.1percent; Expected: 133; Observed: 134.2 (M+1).

Reference: [1] Patent: CN105669548, 2016, A, . Location in patent: Paragraph 0027; 0028
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4078 - 4082[3] Angew. Chem., 2018, vol. 130, # 15, p. 4142 - 4146,5
[4] Chinese Journal of Catalysis, 2016, vol. 37, # 8, p. 1216 - 1221
[5] Organic Letters, 2018, vol. 20, # 7, p. 1987 - 1990
[6] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 571
[7] Patent: US2008/255239, 2008, A1, . Location in patent: Page/Page column 33
[8] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2736 - 2746
[9] Patent: WO2015/50798, 2015, A1, . Location in patent: Page/Page column 69
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  • [ 54664-55-0 ]
Reference: [1] Patent: US2014/200216, 2014, A1,
[2] Patent: US2014/200227, 2014, A1,
[3] Patent: WO2016/168098, 2016, A1,
[4] Patent: WO2016/196244, 2016, A1,
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  • [ 957-68-6 ]
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YieldReaction ConditionsOperation in experiment
99% for 0.0666667 h; Microwave irradiation The method for synthesizing cefpirome sulfuric acid by microwave method according to the present invention,Comprising the steps of:(1) 7-aminocephalosporanic acid (2.72 g, 7-ACA, Compound I, MW272, 0.01 mol) and AE-activity(AEMA, Compound VII, MW 350, 0.011 mol) was mixed and homogeneously ground.(Compound IV, MW 119, 0.011 mol) and concentrated sulfuric acid (10.88 g, 98percent by weight) were added to the solution, followed by the addition of 2,30 g of 2,3-cyclopentenopyridine.(2) 300W microwave reaction for 1 minute,450W microwave reaction for 1 minute,750W microwave reaction for 2 minutes;(3) After completion of the reaction,The reaction residue was added to 29.92 g of deionized water,Mixing and filtering,Take filtrate,The solvent was removed,A white solid,50 & lt; 0 & gt; C for 4 hours under vacuum,That is to get the cefpirome sulfuric acid 5.09g (MW514),Yield 99.0percentPurity 99.9percent or more.
Reference: [1] Patent: CN105646542, 2016, A, . Location in patent: Paragraph 0027; 0040; 0041; 0042; 0043; 0044; 0045
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