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Chemical Structure| 18424-96-9

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Product Details of [ 18424-96-9 ]

CAS No. :18424-96-9
Formula : C5H9NO2
M.W : 115.13
SMILES Code : CN1CCOC(=O)C1
MDL No. :MFCD16659615
InChI Key :NMAIBUJJZUMSPH-UHFFFAOYSA-N
Pubchem ID :519559

Safety of [ 18424-96-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 18424-96-9 ]

* 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 [ 18424-96-9 ]
  • Downstream synthetic route of [ 18424-96-9 ]

[ 18424-96-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 7624-61-5 ]
  • [ 18424-96-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With triethyloxonium fluoroborate In dichloromethane at 20℃;
Stage #2: With Lindlar's catalyst; hydrogen; sodium methylate In ethanol at 25℃; Cooling with ice
General procedure: A solution of carboxylic acid amide (20 mmol) in dichloromethane (10 ml) is admixed with triethyloxonium tetrafluoroborate (4.18 g, 22 mmol) and stirred either (A) overnight at room temperature or (B) for 3 hours on the water bath at 40° C. under argon. Then, the mixture is concentrated in vacuo and the residue is taken up in 20 ml of absolute ethanol. An autoclave cooled in the ice bath is charged with catalyst (1 mol percent) and 10 ml of 2M sodiummethylate solution in ethanol, flushed with argon and filled with the reaction solution in ethanol. 40 bar of hydrogen are then injected in, and the mixture is stirred at 25° C. and a constant pressure until hydrogen absorption is no longer evident (1-12 h). After filtration over Celite, the filtrate is dissolved in 11 ml of 2N hydrochloric acid and washed with diethyl ether, the aqueous phase is rendered basic with 14 ml of 2N NaOH solution, the amine is extracted with diethyl ether, and the combined organic phases are dried over K2CO3. After drawing off the solvent in vacuo, virtually clean amine is obtained. (0186) The catalysts used and yields can be found in Table 6.
References: [1] Patent: US2016/272571, 2016, A1, . Location in patent: Paragraph 185-186.
[2] Advanced Synthesis and Catalysis, 2019, vol. 361, # 1, p. 185 - 191.
  • 2
  • [ 105-59-9 ]
  • [ 18424-96-9 ]
References: [1] Journal of Organic Chemistry, 1987, vol. 52, # 19, p. 4319 - 4327.
[2] Heterocycles, 2010, vol. 80, # 2, p. 855 - 861.
[3] Green Chemistry, 2009, vol. 11, # 6, p. 793 - 797.
[4] Chemistry - A European Journal, 2011, vol. 17, # 45, p. 12596 - 12601.
  • 3
  • [ 109-02-4 ]
  • [ 18424-96-9 ]
YieldReaction ConditionsOperation in experiment
72% With 5.4 wt% Au/CeO2; water; oxygen In 1,4-dioxane at 100℃; for 10 h; Schlenk technique General procedure: A 100-mL Schlenk flask, equipped with a high-vacuumTeflon stopcock was charged with a stir bar and 70 mg of 5.4 wtpercent Au/CeO2 catalyst (3.78 mg, 0.0192 mmol Au).This was followed by the addition of 0.45 mL of ultrapurewater, 2.66 mL of 1,4-dioxane, 1.21 mL of a 404-mM stock solution of N-methylpyrrolidine (0.488 mmol)in 1,4-dioxane, and 0.67 mL of a dodecane (internal standard)stock solution (120 mM) in 1,4-dioxane. The reactionflask was purged through the side arm with oxygenfor 1 min and sealed with the stopcock. The contents ofthe flask were stirred at 80 °C in an oil bath. The moleratio of gold atoms to substrate was 1:25. GC analysis wasperformed as described in Sect. 2.7. At 3.5 h of reactiontime, a 100 percent substrate conversion was achieved with a97 percent yield of N-methyl-2-pyrrolidone. When the reactionof N-methylpyrrolidine was carried out under an air atmosphere,the same procedure was followed as above, butwithout the purge with oxygen gas. Periodic GC analysisof the reaction solution revealed a 97 percent yield of N-methyl-2-pyrrolidone after 10 h of heating at 80 °C. When the reactionwas carried out under an argon atmosphere, using theprocedure outlined in Sect. 2.8, GC analysis of the reactionsolution after 3.5 h of heating at 80 °C revealed a 4 percent yieldof N-methyl-2-pyrrolidone.
References: [1] Catalysis Letters, 2016, vol. 146, # 11, p. 2278 - 2291.
  • 4
  • [ 109-83-1 ]
  • [ 131543-46-9 ]
  • [ 18424-96-9 ]
References: [1] Patent: US5066804, 1991, A, .
[2] Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 188 - 199.
  • 5
  • [ 87688-60-6 ]
  • [ 18424-96-9 ]
References: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 8, p. 1758[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 8, p. 1933 - 1934.
  • 6
  • [ 100180-89-0 ]
  • [ 75-08-1 ]
  • [ 18424-96-9 ]
  • [ 100180-98-1 ]
References: [1] Tetrahedron Letters, 1985, vol. 26, # 15, p. 1853 - 1856.
  • 7
  • [ 109-02-4 ]
  • [ 18424-96-9 ]
  • [ 20721-78-2 ]
  • [ 57503-67-0 ]
References: [1] Tetrahedron Letters, 1990, vol. 31, # 16, p. 2281 - 2282.
  • 8
  • [ 100180-89-0 ]
  • [ 540-63-6 ]
  • [ 18424-96-9 ]
  • [ 100180-97-0 ]
  • [ 98042-18-3 ]
References: [1] Tetrahedron Letters, 1985, vol. 26, # 15, p. 1853 - 1856.
  • 9
  • [ 13200-60-7 ]
  • [ 107-07-3 ]
  • [ 18424-96-9 ]
References: [1] Canadian Journal of Chemistry, 1968, vol. 46, p. 1939 - 1942.
  • 10
  • [ 26294-19-9 ]
  • [ 18424-96-9 ]
References: [1] Justus Liebigs Annalen der Chemie, 1899, vol. 307, p. 203.
  • 11
  • [ 30083-12-6 ]
  • [ 18424-96-9 ]
References: [1] Bulletin de la Societe Chimique de France, 1970, p. 2529 - 2534.
  • 12
  • [ 3053-29-0 ]
  • [ 18424-96-9 ]
References: [1] Bulletin de la Societe Chimique de France, 1970, p. 2529 - 2534.
  • 13
  • [ 26294-19-9 ]
  • [ 108-24-7 ]
  • [ 18424-96-9 ]
References: [1] Journal of the American Pharmaceutical Association. American Pharmaceutical Association, 1956, vol. 45, # 4, p. 197 - 199.
  • 14
  • [ 109-83-1 ]
  • [ 131543-46-9 ]
  • [ 18424-96-9 ]
  • [ 67992-27-2 ]
References: [1] Bulletin de la Societe Chimique de France, 1978, vol. <II>, p. 83 - 88.
 

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