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[ CAS No. 5308-63-4 ]

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Chemical Structure| 5308-63-4
Chemical Structure| 5308-63-4
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CAS No. :5308-63-4 MDL No. :MFCD06658292
Formula : C8H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :135.16 g/mol Pubchem ID :13068663
Synonyms :

Safety of [ 5308-63-4 ]

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 [ 5308-63-4 ]

  • Upstream synthesis route of [ 5308-63-4 ]
  • Downstream synthetic route of [ 5308-63-4 ]

[ 5308-63-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 3510-66-5 ]
  • [ 127-19-5 ]
  • [ 5308-63-4 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: at -78℃; for 2 h;
[Referential Example 35] 5-(5-Methyl-2-pyridyl)-1-(2-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] 1) 1-(5-Methyl-2-pyridyl)ethanone; n-Butyllithium (1.58M solution in hexane, 24 ml) was added to a solution of 2-bromo-5-picoline (5.0 g) in diethylether (100 ml) in 5 minutes at -78°C, and the mixture was stirred for 5 minutes. N,N-Dimethyl acetamide (3.5 ml) was added to the reaction liquid at the same temperature, and the mixture was stirred for 2 hours. Water and ethyl acetate were added to the reaction liquid and the phases were separated, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give 1-(5-methyl-2-pyridyl)ethanone (3.43 g, 87percent) as an oily product. 1H-NMR (400 MHz, CDCl3)δ: 2.42 (3H, s), 2.71 (3H, s), 7.62 (1H, dd, J = 1.59, 7.93 Hz), 7.94 (1H, d, J = 7.93 Hz), 8.50 (1H, s).
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: for 2 h;
1)
1-(5-Methyl-2-pyridyl)ethanone
At -78°C, n-butyllithium (1.58M hexane solution, 24 mL) was added dropwise to 2-bromo-5-picoline (5.0 g) in diethyl ether (100 mL) over 5 minutes, followed by stirring for 5 minutes.
Subsequently, N,N-dimethylacetamide (3.5 mL) was added dropwise to the reaction mixture, followed by stirring for 2 hours.
The reaction mixture was partitioned between water and ethyl acetate.
The organic layer was dried over magnesium sulfate anhydrate.
After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane - ethyl acetate), to thereby give 1-(5-methyl-2-pyridyl)ethanone as an oily product (3.43 g, 87percent).
1H-NMR(400MHz,CDCl3)δ:2.42(3H,s), 2.71(3H,s), 7.62(1H,dd,J=1.59,7.93Hz), 7.94(1H,d,J=7.93Hz), 8.54(1H,s).
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: for 2 h;
2) 1-(5-Methyl-2-pyridyl)-1-ethanone n-Butyllithium (a 1.58 M solution in hexane, 24 mL) was added dropwise to a solution of 2-bromo-5-picoline (5.0 g) in diethyl ether (100 mL) over 5 minutes under cooling to -78°C, and then the resultant mixture was stirred for 5 minutes. N, N-dimethylacetamide (3.5 mL) was added dropwise to the reaction solution, and then the mixture was stirred for 2 hours. Water and ethyl acetate were added to the reaction solution, and the mixture was partitioned. The organic layer was dried over anhydrous magnesium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 1-(5-methyl-2-pyridyl)-1-ethanone (3.43 g, 87percent) as an oily product. 1H-NMR(400MHz, CDCl3)δ: 2.42(3H, s), 2.71(3H, s), 7.62(1H, dd, J=1.59, 7.93Hz), 7.94(1H, d, J=7.93Hz), 8.54(1H, s).
72%
Stage #1: With n-butyllithium In hexanes; diethyl ether at -78 - -40℃; for 0.25 h;
Stage #2: at -78℃; for 2 h;
Stage #3: With ammonium chloride In hexanes; diethyl ether; water
To a solution of 2-bromo-5-methyl pyridine 23 (1.73 g, 10 mmol) in dry ether (20 ml), cooled to -78 0C, was added n-butyllithium (6.25 ml of 1.6M solution in hexanes, 10 mmol, 1 equiv) dropwise. The reaction mixture was allowed to warm to -40 0C for 15 min, then cooled back to -78 0C again. N,N-dimethylacetamide (1.023 ml, 1 1 mmol, 1.1 equiv) was added dropwise and the mixture was stirred at -78 0C for 2h. Saturated aqueous ammonium chloride (10 ml) was added and the organic layer was separated. The aqueous <n="24"/>layer was extracted with ether (3 x 10 ml) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give an oily residue that was subjected to flash column chromatography using (5percent methanol in methylene chloride) to give compound 25 (0.977 g, 72percent) as a yellow oil: TLC R/= 0.48 (silica gel, 25percent EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 8.5-8.48 (broad s, IH), 7.94 (d, J= 8.0 Hz, IH), 7.63-7.60 (m, IH), 2.70 (s, 3H), 2.41 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 200.2, 151.7, 149.7, 137.8, 137.4, 121.7, 26.0, 18.9; HRMS calcd for C8H9NO + Na+ 158.0582; found 158.0580 [M + Na+].

Reference: [1] Inorganic Chemistry, 2018,
[2] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 48
[3] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 30
[4] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 38
[5] Chemistry - A European Journal, 2008, vol. 14, # 2, p. 570 - 581
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 16, p. 4962 - 4966[7] Angew. Chem., 2016, vol. 128, p. 5046 - 5050,5
[8] Patent: WO2008/118327, 2008, A1, . Location in patent: Page/Page column 22-23; Sheet3/13
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12102 - 12106[10] Angew. Chem., 2017, vol. 129, # 40, p. 12270 - 12274,5
[11] New Journal of Chemistry, 2008, vol. 32, # 6, p. 1048 - 1054
  • 2
  • [ 127-19-5 ]
  • [ 5308-63-4 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With n-butyllithium In hexanes; diethyl ether at -78 - -40℃; for 0.25 h;
Stage #2: at -78℃; for 2 h;
Stage #3: With ammonium chloride In hexanes; diethyl ether; water
[00219] l-(5-methylpyridin-2-yl)-ethanone (51)[00220] To a solution of 2-bromo-5 -methyl pyridine 49 (1.73 g, 10 mmol) in dry ether (20 ml), cooled to -78 0C, was added n-butyllithium (6.25 ml of 1.6M solution in hexanes, 10 mmol, 1 equiv) dropwise. The reaction mixture was allowed to warm to -40 0C for 15 min, then cooled back to -78 0C again. N,N-dimethylacetamide (1.023 ml, 11 mmol, 1.1 equiv) was added dropwise and the mixture was stirred at -78 0C for 2h. Saturated aqueous ammonium chloride (10 ml) was added and the organic layer was separated. The aqueous layer was extracted with ether (3 x 10 ml) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give an oily residue that was subjected to flash column chromatography using (5percent methanol in methylene chloride) to give compound 51 (0.977 g, 72percent) as a yellow oil: TLC R/= 0.48 (silica gel, 25percent EtOAc / EPO <DP n="40"/>hexanes); 1HNMR (400 MHz5 CDCl3) δ 8.5-8.48 (m, IH), 7.96-7.93 (d, 3J= 8 Hz, IH)5 7.63- 7.60 (m, IH), 2.70 (s, 3H)5 2.414 (s, 3H); 13C NMR (75 MHz5 CDCl3) δ 200.239, 151.741, 149.704, 137.786, 137.442, 121.663, 26.017, 18.969; HRMS calcd for C8H9NO + Na+ 158.0582; found 158.0580 [M + Na+].
Reference: [1] Patent: WO2007/15929, 2007, A2, . Location in patent: Page/Page column 37-38; 7/22
  • 3
  • [ 18113-81-0 ]
  • [ 5308-63-4 ]
YieldReaction ConditionsOperation in experiment
30% at 110℃; for 50 h; Into a 250 ml three-necked flask, 4.8 g of 5-methyl-2-ethyl-pyridine (40 mmol) and 60 ml of nitrobenzene (1.205 g/ml) are added and refluxed at 110° C. for about 50 h. After the removal of nitrobenzene at a pressure lower than 10 mmHg, a black viscous liquid substance is obtained. The mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:2 is used as an eluent to make silica gel column chromatography on the black viscous liquid substance, and a colorless liquid with a weight of 1.6 g and a yield of 30percent is obtained. The product is identified as 5-methyl-2-acetyl-pyridin by Mass Spectrometry. (0160) Mass Spectrometry MS-EI: 135
Reference: [1] Patent: US9266982, 2016, B2, . Location in patent: Page/Page column 34
  • 4
  • [ 1620-77-5 ]
  • [ 75-16-1 ]
  • [ 5308-63-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 36, p. 9418 - 9426
  • 5
  • [ 1122-72-1 ]
  • [ 5308-63-4 ]
Reference: [1] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
  • 6
  • [ 71777-66-7 ]
  • [ 5308-63-4 ]
Reference: [1] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
  • 7
  • [ 1603-41-4 ]
  • [ 127-19-5 ]
  • [ 5308-63-4 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 15, p. 2551 - 2554
  • 8
  • [ 85279-27-2 ]
  • [ 74-88-4 ]
  • [ 5308-63-4 ]
Reference: [1] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
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