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[ CAS No. 93271-59-1 ]

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Chemical Structure| 93271-59-1
Chemical Structure| 93271-59-1
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CAS No. :93271-59-1 MDL No. :MFCD00716620
Formula : C7H6N2O Boiling Point : 337.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :134.14 g/mol Pubchem ID :-
Synonyms :

Safety of [ 93271-59-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 93271-59-1 ]

  • Upstream synthesis route of [ 93271-59-1 ]
  • Downstream synthetic route of [ 93271-59-1 ]

[ 93271-59-1 ] Synthesis Path-Upstream   1~10

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  • [ 65169-38-2 ]
YieldReaction ConditionsOperation in experiment
98.2% With phosphorus pentachloride In water (c)
Preparation of 2-chloro-3-cyano-4-methylpyridine (Chlorination)
The product of the preceding step, 4-methyl-3-cyano-2-pyridone (40.7 g, 0.304 moles) was added to a stirred solution of POCL3 (140 g, 0.912 moles) and PCl5 (19.0 g, 0.091 moles).
The reaction was heated to reflux (approximately 115° C.) and held under those conditions for two hours.
Excess POCL3 was removed by distillation.
The reaction mixture was then cooled followed by the addition of water (30 mL) water.
The aqueous mixture was extracted with 30 mL methylene chloride.
The extracts were concentrated and 43.2 g was recovered as a tan solid, which was determined to be 2-chloro-3-cyano-4-methylpyridine (4).
mp: 102-104° C.
Yield: 98.2percent
1H NMR: 8.03 (d, J=2 Hz, 1H), 7.6 (d, J=2 Hz, 1H), 2.5 (s, 3H); 13C NMR 156.1, 152.6, 151.8, 124.9, 114.4, 111.8, 20.6
Mass spectrum m/z: 155, 154, 152, 117, 116, 90, 89, 76, 64, 63, 62
FTIR (KBr): 3144, 2979, 2834, 2228, 1653, 1616, 1540, 1484, 1242, 1218, 1173, 819, 607 cm-1
Reference: [1] Patent: US2002/52507, 2002, A1,
[2] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 22
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YieldReaction ConditionsOperation in experiment
89.2% for 1 h; Heating / reflux Example 9 Synthesis of 2-chloro-4-methylpyridine-3-carbonitrile (9)
To a 250 ML flask equipped with a magnetic stirrer was added 10g of 2-hydroxy-4-methyl-3-pyridinylcarbonitrile (8) and 60 ML of phosphorous oxychloride..
The mixture was refluxed for one hour..
The excess POCl3 was distilled under reduced pressure..
The residue was poured into water..
The crystalline material was filtered and dried at to give 10.2g (89.2percent) of (9)..
m.p.: 109-110°C, NMR (DMSO); ppm: 2.56 (s,3H); 7.6 (bs,1H); 8.56 (m,1H).
MS: (EI) m/z M+ 152, 146
88% for 2 h; Reflux A mixture of 2-hydroxy-4-methylpyridine-3-carbonitrile (3.0 g, 22.38 mmol; obtained as described in WO 2011/088201), phosphoryl chloride (6.26 mL, 67.16 mmol) and phosphorus pentachloride (1.4 g, 6.71 mmol) was refluxed for 2 hours. The reaction mixture was cooled to room temperature, and then concentrated under vacuo to dryness. The obtained residue was diluted with aqueous sodium bicarbonate solution. The precipitate thus obtained was collected by filtration and dried to give the title compound as an off-white solid (3.0 g, 88percent). MS(ESI)m/z: 153.1 (M+l) ; 1H NMR CDC13: δ 8.43 (d, J = 5.2 Hz, 1H), 7.22 (d, J = 4.8 Hz, 1H) , 2.8 ( s, 3H
Reference: [1] Patent: EP1064265, 2004, B1, . Location in patent: Page 5
[2] Patent: WO2016/21742, 2016, A1, . Location in patent: Paragraph 0244; 0245
[3] Patent: US6111112, 2000, A,
[4] Research on Chemical Intermediates, 2011, vol. 37, # 6, p. 599 - 604
  • 3
  • [ 5436-21-5 ]
  • [ 107-91-5 ]
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YieldReaction ConditionsOperation in experiment
45%
Stage #1: With ammonium acetate; acetic acid In toluene for 8 h; Reflux; Dean-Stark
Stage #2: With sulfuric acid In ethanol; water at 25 - 50℃; for 3 h;
A mixture of 4,4-dimethoxyl-2-butanone (2.0 g, 15.13 mmol), cyanoacetamide (1.6 g, 18.92 mmol), ammonium acetate (79.3 mg, 1.03 mmol), acetic acid (0.6 mL) in anhydrous toluene (12.4 mL) was refluxed under stirring for 8 h, removing the produced water by Dean-Stark apparatus. When this step was finished, the reaction mixture was evaporated under reduced pressure, the residual oil was cooled to room temperature and EtOH (7.0 mL) was added under stirring at 25 °C. After that, H2SO4 50percent (2.6 mL) was added slowly and the mixture was heated at 50 °C under stirring for 3 h. The reaction mixture was then cooled to 5 °C, and water (1.3 mL) was added slowly. The obtained brown solid was purified by crystallization in EtOH to obtain 2-hydroxy-3-cyano-4-methylpyridine 1 (0.900 g, yield: 45percent); mp: 233-236 °C. 1H NMR (400 MHz, DMSO): δ 12.58 (bs, 1H, NH), 8.04 (d, J = 7.4 Hz, 1H, H6 Py), 6.24 (d, J = 7.4 Hz, 1H, H5 Py), 2.31 (s, 3H, CH3).
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 155 - 171
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  • [ 1025080-30-1 ]
  • [ 410547-37-4 ]
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YieldReaction ConditionsOperation in experiment
75% at 50℃; for 2 h; Preparation 1-2); [140] 4-Methyl-2-oxo-l,2-dihydro-pyridine-3-carbonitrile; [141] To a 10:1 mixture of 2-(3,3-dimethoxy-l-methyl-propylidene)-malononitrile and [(2E)-3-methoxy-l-methylprop-2-en-l-ylidene]malononitrile (38 g, 211 mmol) wis added cone, sulfuric acid (34 mNo., 633 mmol), and the mixture wis stirred for 2 h at 50 0C. The reaction mixture wis cooled to room temperature, and witer (100 mNo. ) was added thereto. The resulting soild compound wis filtered, wished with water (50 mNo. ), and dried to give the title compound (21.1 g, Yield: 75percent).[142] ' H-NMR (DMSO-d , 400 MHz) δ 12.31 (s, IH), 7.65 (d, IH), 6.30 (d, IH), 2.36 (s,63H)
Reference: [1] Patent: WO2008/56898, 2008, A1, . Location in patent: Page/Page column 15
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Reference: [1] Patent: US2010/16376, 2010, A1, . Location in patent: Page/Page column 7
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Reference: [1] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 21
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  • [ 65996-11-4 ]
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1984, vol. 20, # 6, p. 650 - 653[2] Khimiya Geterotsiklicheskikh Soedinenii, 1984, vol. 20, # 6, p. 799 - 802
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  • [ 759-58-0 ]
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1984, vol. 20, # 6, p. 650 - 653[2] Khimiya Geterotsiklicheskikh Soedinenii, 1984, vol. 20, # 6, p. 799 - 802
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1984, vol. 20, # 6, p. 650 - 653[2] Khimiya Geterotsiklicheskikh Soedinenii, 1984, vol. 20, # 6, p. 799 - 802
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Reference: [1] Research on Chemical Intermediates, 2011, vol. 37, # 6, p. 599 - 604
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