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[ CAS No. 24964-64-5 ]

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Chemical Structure| 24964-64-5
Chemical Structure| 24964-64-5
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CAS No. :24964-64-5 MDL No. :MFCD00003344
Formula : C8H5NO Boiling Point : 210.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :131.13 g/mol Pubchem ID :90670
Synonyms :

Safety of [ 24964-64-5 ]

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 [ 24964-64-5 ]

  • Upstream synthesis route of [ 24964-64-5 ]
  • Downstream synthetic route of [ 24964-64-5 ]

[ 24964-64-5 ] Synthesis Path-Upstream   1~18

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  • [ 24964-64-5 ]
  • [ 64407-07-4 ]
Reference: [1] Catalysis Science and Technology, 2015, vol. 5, # 4, p. 2406 - 2417
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  • [ 24964-64-5 ]
  • [ 115-20-8 ]
  • [ 244621-31-6 ]
Reference: [1] Patent: US6509335, 2003, B1,
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  • [ 64-17-5 ]
  • [ 24964-64-5 ]
  • [ 2463-16-3 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In water at 20℃; for 5 h; General procedure: A mixture of bromine chloride resin and K2CO3 in MeOH–H2O (8:2) 3 mL was placed in a round-bottom flask fitted with amagnetic stirrer. To this, the aldehyde (1 mmol, 1 equiv) was added dropwise, and the reaction mixture stirred at r.t. The progress of the reaction was monitored by TLC. After completionof the reaction the mixture was filtered, and the filtrate was extracted with Et2O. The ether layer was washed with H2O, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography, if required, over silicagel (60–120 mesh) using a mixture of PE and EtOAc (9:1) as eluent.
Reference: [1] Synlett, 2016, vol. 27, # 9, p. 1344 - 1348
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2070 - 2072
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  • [ 1877-77-6 ]
YieldReaction ConditionsOperation in experiment
70% With lithium aluminium tetrahydride In tetrahydrofuranHeating / reflux Lithium aluminum hydride (1.0 M in THF, 29.9 mL, 29.9 mmol) was added slowly to a solution of 3-cyanobenzaldehyde (1.12 g, 9.25 mmol) in anhydrous THF (25.0 mL) at room temperature under argon and the mixture was stirred at reflux (overnight). The reaction mixture was cooled to room temperature and quenched by addition of ice and NaOH (aq. 3.0 N, 10.0 mL). The mixture was extracted with chloroform (3 x 80 mL) and the combined organic phase was washed with brine (2 x 20 mL) and dried (Na2SO4). The solvent was evaporated and the residue was purified by silica gel column chromatography to yield [3- (hydroxymethyl)phenyl] amine as colorless oil (70percent yield). [1H NMR (CDCl3): δ 7.26-7.22 (m, IH), 7.21-7.19 (m, IH), 7.16-7.14 (m, IH), 7.12-7.09 (m, IH), 4.55 (d, 2H, J = 6.0 Hz), 3.71 (d, 2H, /= 8.0 Hz); 13C NMR (CDCl3): δ 142.7, 142.0, 128.6, 126.0, 125.5, 125.4, 64.4, 46.1; FAB-MS m/z 138.1 (MH+).] Reaction of this material according to general procedure G provided 23f in 38percent yield. 1H NMR (CDCl3): δ 7.22 (s, IH), 7.20-7.18 (m, 2H), 7.11-7.09 (m, IH), 6. 98 (d, IH, 7 = 8.4 Hz), 6.91 (d, IH, 7 = 8.4 Hz), 4.60 (s, 2H), 4.57 (s, 2H), 4.06 (s, 2H), 4.01 (d, 3H, 7 = 1.2 Hz), 3.80 (d, 3H, 7 = 1.2 Hz); 13C NMR (CDCl3): δ 166.8, 152.2, 147.2, 141.9, 137.1, 134.5, 128.8, 127.0, 126.6, 126.1, 124.7, 117.8, 116.5, 64.6, 62.4, 56.7, 48.5, 46.2; FAB-MS m/z 314.1 (MH+).
Reference: [1] Patent: WO2009/26248, 2009, A2, . Location in patent: Page/Page column 52; 53
  • 5
  • [ 201230-82-2 ]
  • [ 100-47-0 ]
  • [ 24964-64-5 ]
  • [ 874-89-5 ]
  • [ 7468-67-9 ]
  • [ 874-97-5 ]
Reference: [1] Chemistry Letters, 1987, p. 1113 - 1116
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  • [ 42287-97-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 437 - 450
[2] Die Pharmazie, 1973, vol. 28, # 11, p. 724 - 729
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  • [ 141-82-2 ]
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  • [ 16642-93-6 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: at 100℃; for 4 h;
Stage #2: With hydrogenchloride In water at 20℃;
General procedure: 3-Cyanobenzaldehyde (11a) or 4-cyanobenzaldehyde (11b) (15 mmol) and malonic acid (30 mmol) were dissolved in pyridine (30 mL). Piperidine (3.0 mmol) was added and the reaction was heated for 4 h at 100 °C. The reaction was cooled to room temperature and 5 M HCl (25 mL) was added slowly. The resulting white precipitate was collected by filtration, washed with water and dried to give (E)-3-cyanocinnamic acid (12a) or (E)-4-cyanocinnamic acid (12b) in yields of 81percent and 78percent, respectively.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 1560
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2021 - 2034
[4] Patent: WO2006/123725, 2006, A1, . Location in patent: Page/Page column 40
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  • [ 16642-93-6 ]
Reference: [1] Patent: US4665189, 1987, A,
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  • [ 126534-87-0 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 18, p. 5690 - 5698
[2] RSC Advances, 2013, vol. 3, # 3, p. 895 - 899
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  • [ 24964-64-5 ]
  • [ 34231-22-6 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4786 - 4797
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 2, p. 251 - 259
[3] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5438 - 5443
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S404 - S406
[5] Organic Mass Spectrometry, 1993, vol. 28, p. 67 - 70
[6] Journal of Catalysis, 2011, vol. 284, # 2, p. 176 - 183
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  • [ 24964-64-5 ]
  • [ 226070-69-5 ]
Reference: [1] Patent: WO2005/18557, 2005, A2,
  • 12
  • [ 24964-64-5 ]
  • [ 550364-01-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4645 - 4648
  • 13
  • [ 24964-64-5 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: US2017/362192, 2017, A1,
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  • [ 24964-64-5 ]
  • [ 220364-34-1 ]
Reference: [1] Patent: WO2005/18557, 2005, A2,
  • 15
  • [ 109-01-3 ]
  • [ 24964-64-5 ]
  • [ 859850-90-1 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;
Stage #2: With sodium carbonate In dichloromethane; water
Preparation 14: 1-[3-(4-WlethyI-piperazin-1-ylmethyl)-phenyI]-ethanone; STEP A; A mixture of 3-formyl-benzonitrile (1.5 g, 11.45 mmol), N-methyl piperazine (1.49 g, 14.9 mmol) and NaBH(OAc)3 (3.63 g, 17.18 mmol) in DCM (75 ml) and CH3COOH (0.851 ml, 14.9 mmol) was stirred overnight at room temperature, then diluted with DCM and washed with 1 M Na2CO3. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 97:3:0.5) to give 1.7 g of 3-(4- methyl-piperazin-1-ylmethyl)-benzonitrile. Y= 70percent
70%
Stage #1: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;
Stage #2: With sodium carbonate In dichloromethane; water
STEP A
A mixture of 3-formyl-benzonitrile (1.5 g, 11.45 mmol), N-methyl piperazine (1.49 g, 14.9 mmol) and NaBH(OAc)3 (3.63 g, 17.18 mmol) in DCM (75 ml) and AcOH (0.851 ml, 14.9 mmol) was stirred at RT overnight and then diluted with DCM and washed with 1 M Na2CO3.
The organic phase was dried over Na2SO4 and evaporated under vacuum.
The crude product was purified by column chromatography (eluent: DCM/MeOH/NH4OH 97:3:0.5) to give 3-(4-methyl-piperazin-1-yl-methyl)-benzonitrile (1.7 g).
Y=70percent
Reference: [1] Patent: WO2007/113249, 2007, A2, . Location in patent: Page/Page column 60-61
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 822 - 839
[3] Patent: EP2033956, 2009, A1, . Location in patent: Page/Page column 13
[4] Patent: WO2006/130075, 2006, A1, . Location in patent: Page/Page column 25-26
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  • [ 515162-19-3 ]
Reference: [1] Patent: WO2006/130075, 2006, A1,
  • 17
  • [ 24964-64-5 ]
  • [ 1003708-42-6 ]
  • [ 77976-07-9 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 2, p. 339 - 344
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  • [ 24964-64-5 ]
  • [ 1286693-23-9 ]
Reference: [1] Patent: WO2011/44307, 2011, A1,
[2] Patent: WO2014/152029, 2014, A2,
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