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[ CAS No. 873-62-1 ]

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Chemical Structure| 873-62-1
Chemical Structure| 873-62-1
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CAS No. :873-62-1 MDL No. :MFCD00002252
Formula : C7H5NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :119.12 g/mol Pubchem ID :13394
Synonyms :

Safety of [ 873-62-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 873-62-1 ]

  • Upstream synthesis route of [ 873-62-1 ]
  • Downstream synthetic route of [ 873-62-1 ]

[ 873-62-1 ] Synthesis Path-Upstream   1~55

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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: at 50℃; for 70 h;
Stage #2: With hydrogenchloride In methanol; water
Example 49; 3-Hydroxybenzamide (49a). 3-Cyanophenol (295 mg, 2.48 mmol, 100 mol-percent) and NaBO3 - 4 H2O (1146 mg, 7.45 mmol, 300 mol-percent) in H2O (8 ml_) were heated to 50 0C and MeOH (14 ml_) was added until mixture was clear. The mixture was stirred at 50 0C for 70 hours and excess MeOH was evaporated and the pH of remaining mixture was adjusted to 5 with cone. HCI (aq). Mixture was extracted with CH2CI2 (12 ml_) and with EtOAc (5x15 ml_). Organic phases were combined, washed with brine (25 ml_) and dried over Na2SO4. Filtering and evaporation of solvents gave 49a as spectro- scopically pure white solid (183 mg, 54percent): mp 165-168 0C; Rf (50percent EtOAc in hex) 0.10.
Reference: [1] RSC Advances, 2015, vol. 5, # 16, p. 12152 - 12160
[2] Tetrahedron, 1989, vol. 45, # 11, p. 3299 - 3306
[3] ChemMedChem, 2010, vol. 5, # 2, p. 213 - 231
[4] Patent: WO2008/129129, 2008, A1, . Location in patent: Page/Page column 66
  • 3
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Reference: [1] Synthesis, 2003, # 2, p. 243 - 246
  • 4
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YieldReaction ConditionsOperation in experiment
92% With dihydrogen peroxide In ethanol; water at 20℃; General procedure: In a 50 mL round-bottomed flask, a mixture of arylboronic acid(1 mmol), H2O2 (30percent aq, 0.2 mL), ZnO nanocatalyst (5 molpercent; sampleZnO-1) and 2 mL of water were stirred at room temperature under aerobic condition. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was diluted with 20 mL of water and extracted with (3×20) mL of diethyl ether. The combined organic layer was washed with brine and dried over Na2SO4. The solvent was removed in a rotary evaporator under reduced pressure. The crude product was purified by column chromatography (hexane/ ethylacetate, 9:1) on silica (100–200mesh) to get the desired product. The products were identified by 1HNMR and 13C NMR.
89% With air; Ru(at)imine-nanoSiO2 catalyst In water; isopropyl alcohol at 30℃; for 0.8 h; Green chemistry General procedure: A 50mL round bottom flask was charged with arylboronic acid (1mmol), 5mg Ru catalyst and 4ml iPrOH:H2O (1:1). The reaction mixture was stirred at room temperature under aerobic condition. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was diluted with 20mL of water and extracted with diethyl ether. The combined organic layers were washed with brine and dried over by anhydrous Na2SO4 and evaporated in a rotary evaporator under reduced pressure. The crude was purified by column chromatography on silica gel (hexane:ethyl acetate, 9:1) to afford the desired product. The purity of the compound was confirmed by 1H NMR, 13C NMR.
88% With dihydrogen peroxide In water at 20℃; for 0.166667 h; Green chemistry General procedure: In a 50mL round-bottomed flask, a mixture of arylboronic acid (1mmol), H2O2 (30percent aq, 0.2mL), bio-silica (5mg) and 2mL of water was added and stirred at room temperature in aerobic condition. The reaction was monitored by TLC. After completion of the reaction the reaction mixture was diluted with 20mL of water and extracted with (3×20) mL of diethylether and the combined organic layer was washed with brine and dried over by Na2SO4 and evaporated in a rotary evaporator under reduced pressure. The crude was purified by column chromatography (hexane/ethylacetate, 9:1) on mesh silica (100–200) to get the desired product. The products were confirmed by 1H NMR, 13C NMR, FT-IR spectroscopy and mass spectrometry.
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5236 - 5241
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 2013 - 2019
[3] Applied Catalysis A: General, 2018, vol. 562, p. 58 - 66
[4] Tetrahedron Letters, 2016, vol. 57, # 36, p. 4050 - 4052
[5] Tetrahedron Letters, 2015, vol. 56, # 14, p. 1780 - 1783
[6] Chemistry Letters, 2016, vol. 45, # 3, p. 268 - 270
[7] ACS Catalysis, 2017, vol. 8, # 6, p. 5313 - 5322
  • 5
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YieldReaction ConditionsOperation in experiment
91% With acetic acid; hydroxylamine-O-sulfonic acid In water at 50℃; for 6 h; General procedure: In a 10 mL round bottom flask at 0 °C, aldehyde (1.0 mmol, 1.0 equiv) and NH2OSO3H (1.1 mmol, 1.1 equiv) were dissolved in 4 mL of H2O with acetic acid (1.0 mmol, 1 equiv). The reaction was stirred at 50 °C for 6 h or until complete conversion by TLC. The reaction was quenched with aqueous 10percent NaHCO3 (1 mL) and the resulting mixture was extracted with EtOAc (3*10 mL), dried (Na2SO4), filtered, and concentrated by rotary evaporation to afford the crude product. The product was directly characterized unless traces of impurities required purification by automated silica gel flash chromatography (three examples).
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 10, p. 1000 - 1006
[2] Tetrahedron, 2002, vol. 58, # 52, p. 10323 - 10328
[3] European Journal of Organic Chemistry, 2006, # 11, p. 2513 - 2516
[4] Liebigs Annalen der Chemie, 1984, vol. 1984, # 3, p. 409 - 425
[5] Synlett, 1999, # 10, p. 1569 - 1570
[6] RSC Advances, 2014, vol. 4, # 27, p. 13782 - 13787
[7] Tetrahedron Letters, 2016, vol. 57, # 34, p. 3844 - 3847
[8] Synlett, 2000, # 11, p. 1599 - 1600
[9] Synthetic Communications, 1992, vol. 22, # 14, p. 2125 - 2128
[10] Synthesis, 2003, # 2, p. 243 - 246
[11] Journal of Organic Chemistry, 1982, vol. 47, # 11, p. 2101 - 2108
[12] Synthetic Communications, 1983, vol. 13, # 12, p. 999 - 1006
[13] Synthesis, 2005, # 5, p. 787 - 790
[14] Dalton Transactions, 2008, # 6, p. 738 - 741
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YieldReaction ConditionsOperation in experiment
77% With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Inert atmosphere General procedure: In an oven-dried two-necked 50 mLround-bottomed flask, equipped with a stirring bar, a solution of the oxime(1.0 mmol) and 2-NO2-C6H4-SO3XY(1.5 mmol) dissolved in anhydrous CH2Cl2 (5.0 mL) wasplaced under the atmosphere of nitrogen. The reaction mixture was stirred atroom temperature for 5 min, then DBU (2.5 mmol) was added drop wise over 2 min.The reaction mixture became a clear homogeneous solution after addition of DBU.The reaction was monitored by TLC. The reaction mixture was diluted with EtOAcand washed with water (2×5 mL) followed by brine (2×5 mL) upon completeconsumption of the starting material. Product was purified by columnchromatography.Furthermore, the by-product Oxymacould be readily recovered by acidifying the aqueous layer, and then extractingwith ethyl acetate. The Oxyma thus recovered can then be reused to regeneratethe sulfonate ester of Oxyma, which can be further used for a separate batch ofreaction.
Reference: [1] Synthesis, 2005, # 5, p. 787 - 790
[2] Synthesis, 2003, # 2, p. 243 - 246
[3] Tetrahedron Letters, 2007, vol. 48, # 14, p. 2639 - 2643
[4] Tetrahedron Letters, 2013, vol. 54, # 33, p. 4397 - 4400
[5] Journal of the Chemical Society, 1937, p. 479,482
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4478 - 4482[2] Angew. Chem., 2017, vol. 129, # 16, p. 4549 - 4553,5
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[4] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
[5] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10694 - 10695
[6] Organic Letters, 2017, vol. 19, # 11, p. 3033 - 3036
  • 8
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With cesium fluoride In N,N-dimethyl-formamide at 60℃; for 1 h; Inert atmosphere
Stage #2: With water In N,N-dimethyl-formamideInert atmosphere
General procedure: To a solution of [2-(phenoxy)-ethyl]-trimethyl-silane (Table-3, entry-1) (195mg, 1.0 mmol) in dry DMF (2 ml) was added cesium fluoride (576 mg, 3.0 mmol) and heated at 60°C for 1 h. Reaction mass was diluted with water and extracted with ethyl acetate (3 x 20 ml). The combined organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to give phenol 92mg (93percent yield). Phenols of Table-3 are commercially available from Aldrich and its identity was confirmed by comparison of 1H NMR data with authentic sample.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5338 - 5341
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[2] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
[3] Organic Letters, 2012, vol. 14, # 14, p. 3688 - 3691
  • 10
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Reference: [1] Inorganica Chimica Acta, 2016, vol. 444, p. 159 - 165
[2] Tetrahedron Letters, 1982, vol. 23, # 25, p. 2605 - 2608
[3] Chemical Communications, 2006, # 9, p. 1012 - 1014
[4] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 13995 - 14006
[5] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2855 - 2861
[6] Chinese Journal of Catalysis, 2015, vol. 36, # 7, p. 1086 - 1092
[7] Catalysis Letters, 2015, vol. 145, # 4, p. 1014 - 1021
  • 11
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YieldReaction ConditionsOperation in experiment
90% at 105℃; for 6.5 h; General procedure: To a stirred solution of aryl methyl ether (20 mmol) and 47percent aqueous HBr (4.5 mmol equiv. of substrate) added Aliquat-336 (10 wt. percent of substrate) in a single lot. The resulting reaction mixture was heated at 105±5 °C, and the progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to room temperature and quenched by adding water (25 ml). The resulting reaction mass was extracted with 3x30 ml ethyl acetate. Ethyl acetate layer washed twice with 20 ml of water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane system.
Reference: [1] Synthetic Communications, 2013, vol. 43, # 24, p. 3272 - 3280
[2] Tetrahedron Letters, 2004, vol. 45, # 19, p. 3729 - 3732
[3] Synthetic Communications, 2011, vol. 41, # 12, p. 1852 - 1857
[4] Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9719 - 9721
  • 12
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Reference: [1] Organic Letters, 2018, vol. 20, # 3, p. 708 - 711
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5338 - 5341
  • 13
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Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
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Reference: [1] Organic Letters, 2017, vol. 19, # 10, p. 2670 - 2673
  • 15
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Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 11, p. 1815 - 1818
  • 16
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Reference: [1] Synthesis, 1998, # 3, p. 329 - 332
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 34, p. 14056 - 14069,14
[2] Journal of the American Chemical Society, 2012, vol. 134, # 34, p. 14056 - 14069
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Reference: [1] Green Chemistry, 2009, vol. 11, # 8, p. 1112 - 1114
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Reference: [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 4, p. 643 - 648
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Reference: [1] Australian Journal of Chemistry, 1983, vol. 36, # 12, p. 2473 - 2482
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10567 - 10571
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Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 667 - 672
  • 23
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Reference: [1] Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 513 - 516
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1877, vol. <2> 16, p. 221
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 667 - 672
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2821 - 2826
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Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 667 - 672
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Reference: [1] Synthesis, 2003, # 2, p. 243 - 246
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Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 10, p. 2799 - 2805
  • 29
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Reference: [1] Journal of the American Chemical Society, 1993, vol. 115, # 23, p. 10722 - 10727
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Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 8, p. 2537 - 2543
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Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 2, p. 523 - 530
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Reference: [1] Tetrahedron Letters, 1985, vol. 26, # 23, p. 2739 - 2742
[2] Tetrahedron Letters, 1985, vol. 26, # 23, p. 2739 - 2742
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 14, p. 4204 - 4209
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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 13, p. 4462 - 4465
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Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 13, p. 4460 - 4461
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Reference: [1] Chemical Communications, 2008, # 38, p. 4634 - 4636
  • 38
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Reference: [1] Chemische Berichte, 1887, vol. 20, p. 2955
  • 39
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Reference: [1] Chemical & Pharmaceutical Bulletin, 1989, vol. 37, # 7, p. 1922 - 1924
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Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1997, # 2, p. 179 - 183
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  • [ 767-00-0 ]
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  • [ 108-95-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 1135 - 1142
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  • [ 108-88-3 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 23, p. 7119 - 7120
  • 43
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Reference: [1] Organic Letters, 2012, vol. 14, # 11, p. 2818 - 2821
[2] Organic Letters, 2012, vol. 14, # 11, p. 2818 - 2821
  • 44
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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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YieldReaction ConditionsOperation in experiment
97% With hydrogen In methanol at 25℃; Under a nitrogen atmosphere,10.0 g of compound 1 and 1 g of Raney nickel were placed in a 500 ml flask,200ml of methanol was added to replace the hydrogen atmosphere, and the system was reacted at room temperature overnight.The reaction was monitored by TLC, the reaction was filtered through celite,The filtrate was concentrated to give compound 2 as a white solid 10g, 97percent yield.HPLC analysis showed a purity of 97percent and was used in the next reaction without further isolation and purification.
97% With hydrogen In methanol at 20℃; for 10 h; In a 1L round-bottomed flask was added 180 3-hydroxybenzonitrile (9) (10g, 84mmol, 1.0 eq) in 181 MeOH (200mL) to give a yellow solution. The reaction vessel was purged with nitrogen. 182 Rany-Ni (0.719g, 8.39mmol, 0.1 eq) was added. The reaction vessel was purged with hydrogen. The reaction was heated to rt with stirring on for 10h. The reaction mixture was filtered through celite with MeOH. The mixture was concentrated by rotovap. 183 DCM (20mL) was added. The reaction mixture was filtered through sintered glass funnel to give 184 3-(aminomethyl)phenol (10) (10g, 97percent yield) as white solid. m.p. 170–172°C; ESI-MS m/z: 124.65, [M+H]+.
73% With sodium hydroxide; LiAlH4; trifluoroacetic acid In tetrahydrofuran; diethyl ether; water; acetonitrile A.
3-(Aminomethyl)phenol
3-Hydroxybenzonitrile (1.2 g, 0.010 mol) was dissolved in anhydrous diethyl ether (30 mL) and LiAlH4 (1M solution in THF, 10 mL, 0.010 mol) was added dropwise over 30 minutes at room temperature.
The mixture was stirred at room temperature for 2 hours and cooled to 0°C, and 15percent NaOH (50 mL) was added.
The mixture was neutralized with TFA.
Half of the crude mixture was purified by preparative HPLC (YMC S-10 ODS colum, 50 X 500 mm; solvent A, 0.1percent TFA in 90percent water, 10percent acetonitrile; solvent B, 0.1percent TFA in 10percent water, 90percent acetonitrile: 0percent B in 40 minutes, flow rate 50 mL/minute; UV monitored at 220 nm).
Fractions containing the desired product were combined, concentrated and lyophilized to provide compound A (450 mg, 73percent), MS: (M+H)+ 124+.
Reference: [1] Patent: CN107266341, 2017, A, . Location in patent: Paragraph 0045-0048
[2] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 757 - 770
[3] Patent: EP696593, 1996, A2,
[4] Journal of the Chemical Society - Series Chemical Communications, 1986, vol. No. 2, p. 158 - 160
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Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1319 - 1321
[2] Patent: US2017/298081, 2017, A1,
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  • [ 97582-88-2 ]
Reference: [1] Patent: US5731477, 1998, A,
[2] Patent: US5731477, 1998, A,
  • 48
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  • [ 97582-88-2 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 6, p. 2075 - 2084
  • 49
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  • [ 211172-52-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1319 - 1321
[2] Patent: WO2011/106986, 2011, A1,
  • 50
  • [ 873-62-1 ]
  • [ 189680-06-6 ]
YieldReaction ConditionsOperation in experiment
22% at 20℃; for 18 h; Step 1 : 4-Bromo-3-cyanophenolTo a mixture of 3-cyanophenol (3.2 g, 26.8 mmol) in glacial acetic acid (20 ml) was added a solution of bromine (4.2 g, 23.3 mmol) in acetic acid (5 ml) dropwise over 5 minutes. The mixture was stirred at room temperature for 18 hours. The mixture was filtered. The filtrate was added to water (100 ml) containing a few mg of sodium thiosulfate. The insoluble material was collected and the filter cake was added to warm methanol (15 ml) and was filtered through celite. The filtrate was slowly diluted with water and the precipitate was collected and dried to give the title compound, 183-5°C, mp (1.0 g, 22percent).
Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 2, p. 120 - 124
[2] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 80
[3] Patent: WO2004/35556, 2004, A1, . Location in patent: Page 95
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Reference: [1] Molecules, 2014, vol. 19, # 3, p. 3401 - 3416
[2] Synthetic Communications, 2004, vol. 34, # 5, p. 751 - 758
[3] Heterocyclic Communications, 2011, vol. 17, # 1-2, p. 10 - 16
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  • [ 189680-06-6 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[2] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
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YieldReaction ConditionsOperation in experiment
26% With sodium hydrogencarbonate; sodium sulfate; triethylamine In dichloromethane; chloroform; water; acetonitrile REFERENCE EXAMPLE 18
3-Morpholinobenzonitrile
3-Cyanophenol (1.77 g, 14.9 millimole) and triethylamine (6.30 ml, 45.2 millimole) were dissolved with methylene chloride (75 ml), and the solution is stirred under an argon gas environment at -10 degrees Celsius.
The solution of trifluoroacetic andydride (3.79 ml, 22.5 millimole), dissolved with methylene chloride (15 ml), is dripped, and the mixture is stirred for 1.5 hours.
After completion of the reaction, the solvent is removed under reduced pressure.
A sodium hydrogencarbonate aqueous solution is added to the obtained concentrated residuum, and extraction is performed with methylene chloride.
The organic layer is washed with a saturated saline solution, and dried using sodium sulfate.
After the desiccant is separated through filtration, the filtrate is concentrated.
The obtained concentrated residuum is purified using silica gel column chromatography (chloroform/methanol=100), and oily material is obtained.
The obtained oily material is dissolved with acetonitrile (40 ml).
Morpholine (33.0 ml, 378 millimole) is added to the solution, and the solution is stirred for 3 days while the solvent is refluxed.
The solvent and the reagent which did not react were removed under reduced pressure.
Water is added to the obtained concentrated residuum, and extraction is performed using chloroform.
After the organic layer is dried (sodium sulfate), the desiccant is separated through filtration, and the filtrate is concentrated.
The obtained concentrated residuum is purified using silica gel column chromatography (eluted with chloroform/hexane=1/2), and the subject compound is obtained as oily material (0.74 g, 26percent).
1H-NMR (CDCl3) δ (ppm): 3.15-3.19 (4H, m), 3.83-3.88 (4H, m), 7.09-7.18 (3H, m), 7.34 (1H, dd, J=7.6 Hz, 7.6 Hz).
26% With sodium bicarbonate; triethylamine; trifluoroacetic anhydride In dichloromethane; water; acetonitrile REFERENCE EXAMPLE 18
3-Morpholinobenzonitrile
3-Cyanophenol (1.77 g, 14.9mmol) and triethylamine (6.30 ml, 45.2 mmol) were dissolved in methylene chloride (75 ml) and stirred at -10° C. in an argon gas atmosphere.
A solution of trifluoroacetic anhydride (3.79 ml, 22.5 mmol) dissolved in methylene chloride (15 ml) was added dropwise thereto, and after the addition was completed, the mixture was stirred for 1.5 hours.
After the reaction was completed, the solvent was removed under reduced pressure, and an aqueous solution of sodium hydrogen carbonate was added to the resulting concentrated residue and the mixture was extracted with methylene chloride.
The organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate.
The drying agent was filtered off and the filtrate was concentrated.
The resulting concentrated residue was purified by silica gel column chromatography (chloroform/methanol=100) to give oily substances.
The resulting oily substances were dissolved in acetonitrile (40 ml).
Morpholine (33.0 ml, 378 mmol) was added thereto and the mixture was stirred for 3 days under heating at reflux.
The solvent and unreacted reagents were distilled off under reduced pressure, water was added to the concentrated residue, and the mixture was extracted with chloroform.
The organic layer was dried (over sodium sulfate), the drying agent was filtered off, and the filtrate was concentrated.
The resulting concentrated filtrate was purified by silica gel column chromatography (eluent: chloroform/hexane=1/2) to give the title compound (0.74 g, 26percent) as oily substances.
1 H-NMR (CDCl3) δ (ppm): 3.15-3.19(4H, m), 3.83-3.88(4H, m), 7.09-7.18(3H, m), 7.34(1H, dd, J=7.6 Hz, 7.6 Hz).
Reference: [1] Patent: US2002/193389, 2002, A1,
[2] Patent: US6127541, 2000, A,
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  • [ 214360-46-0 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917
[2] Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917
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  • [ 873-62-1 ]
  • [ 51786-11-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1319 - 1321
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