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Product Details of [ 35708-19-1 ]

CAS No. :35708-19-1 MDL No. :MFCD01366532
Formula : C14H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ODDHBYXHXZCAGQ-UHFFFAOYSA-N
M.W : 227.26 Pubchem ID :607074
Synonyms :

Safety of [ 35708-19-1 ]

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 [ 35708-19-1 ]

* 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 [ 35708-19-1 ]
  • Downstream synthetic route of [ 35708-19-1 ]

[ 35708-19-1 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 35708-19-1 ]
  • [ 75-16-1 ]
  • [ 6267-02-3 ]
YieldReaction ConditionsOperation in experiment
81% at 0℃; 20.0 g (88.00 mmol) of the intermediate (A) synthesized in the above step 1 was suspended in terrahydrofuran (293 ml), and then 102.7 ml of methylmagnesium bromide (3M) was slowly added dropwise at 0 ° C. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled under reduced pressure. 100 ml of sulfuric acid diluted to 10percent in distilled water was added to the distillation product, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and recrystallized from dichloromethane and hexane to obtain 15.0 g (yield: 81percent) of the intermediate product (B).
Reference: [1] Patent: KR2016/102142, 2016, A, . Location in patent: Paragraph 0215; 0223; 0224
[2] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081
  • 2
  • [ 35708-19-1 ]
  • [ 6267-02-3 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 1, p. 358 - 384
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 2976 - 2993
[3] Patent: WO2011/93609, 2011, A1,
[4] Patent: WO2012/39561, 2012, A1,
[5] Patent: WO2013/45411, 2013, A1,
[6] Patent: WO2014/165307, 2014, A2,
[7] Patent: CN105585577, 2016, A,
[8] Patent: KR2018/30860, 2018, A,
[9] Patent: US2018/166636, 2018, A1,
  • 3
  • [ 35708-19-1 ]
  • [ 100-58-3 ]
  • [ 20474-15-1 ]
YieldReaction ConditionsOperation in experiment
56% With sulfuric acid In tetrahydrofuran A Grignard reaction was performed by using Intermediate I-3-1 (2 g, 0.009 mol) and phenyl magnesium bromide (2.07 g, 0.012 mol) to obtain diphenyl(2-(phenylamino)phenyl)methanol. Without separating diphenyl(2-(phenylamino)phenyl)methanol, 30 mL of sulfuric acid was added thereto to obtain Intermediate I-5-2 (1.6 g, 56percent).
Reference: [1] Patent: US2017/25620, 2017, A1, . Location in patent: Paragraph 0324; 0327; 0328
  • 4
  • [ 35708-19-1 ]
  • [ 20474-15-1 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 3202
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 2976 - 2993
[3] Chemistry - An Asian Journal, 2015, vol. 10, # 6, p. 1402 - 1409
[4] Chemical Communications, 2016, vol. 52, # 52, p. 8149 - 8151
[5] Journal of Materials Chemistry C, 2016, vol. 4, # 33, p. 7869 - 7874
[6] Patent: US2017/5275, 2017, A1,
  • 5
  • [ 35708-19-1 ]
  • [ 1211-19-4 ]
Reference: [1] Journal of the American Chemical Society, 1933, vol. 55, p. 4294,4297, 4298
  • 6
  • [ 17763-70-1 ]
  • [ 62-53-3 ]
  • [ 35708-19-1 ]
YieldReaction ConditionsOperation in experiment
99% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 120℃; Inert atmosphere To a solution of bromide (or triflate) (1 equiv) in toluene (0.1 M) was added aniline (1.2 equiv), Cs2CO3 (1.4 equiv) BINAP (0.08 equiv), and Pd(OAc)2 (0.05 equiv) at room temperature. The reaction mixture was allowed to stir at 120 °C for 4-48 h. Once the reaction appeared to be complete by consumption of the bromide (or triflate) by TLC analysis, the mixture was allowed to cool to room temperature, diluted with EtOAc, washed with 2M aq HCl (2x), brine, and dried over sodium sulfate. The solution was concentrated, loaded on silica gel, and purified by silica gel chromatography.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1464 - 1468
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2311 - 2323
[3] Journal of Organic Chemistry, 2009, vol. 74, # 13, p. 4720 - 4726
  • 7
  • [ 67-56-1 ]
  • [ 91-40-7 ]
  • [ 35708-19-1 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: for 0.166667 h; Cooling with ice
Stage #2: at 0 - 90℃; for 12 h;
Preparation of Compound 1-1 [95] After 2-(phenylamino)benzoic acid (50 g, 0.23 mol) was dissolved in MeOH (1 L) and put into an ice bath, the mixture was stirred for 10 minutes. After slowly adding SOCl2 (60 mL, 0.58 mol) thereto at 0 , the mixture was stirred under reflux for 12 hours at 90 . Upon completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Compound 1-1 (47 g, 92percent) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
92% at 0 - 90℃; for 12 h; Reflux 2-(phenylamino)benzoic acid (50g, 0.23mol) was dissolved in MeOH 1L, placed in an ice bath and then stirred at 0°C for 10 minutes. SOCl2 (60mL, 0.58mol) was slowly added at 0°C and the mixture was stirred under reflux at 90°C for 12 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-1 (47g, 92percent).
92% at 0 - 90℃; for 12 h; 2-(phenylamino)benzoic acid (50 g, 0.23 mol) was dissolved in methanol (1 L), put in an ice bath and stirred for ten minutes. After slowly adding SOCI2 (60 ml_, 0.58 mol) thereto at 0°C, the mixture was stirred under reflux for 12 hours at 90°C.Upon completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. After drying the organic layer with magnesium sulfate and removing the solvent by a rotary type evaporator, 2-(phenylamino) methyl benzoate (47 g, 92percent) was obtained through purification by column chromatography using ethyl acetate as developing solvent.
90% for 5 h; 2.5 grams (g) (0.12 moles (mol)) of 2-(phenylamino)benzoic acid, 1.39 g (0.13 mol) of thionyl chloride, and 50 milliliters (ml) of methanol were added to a flask, and these reactants were allowed to react for 5 hours. After the reaction was completed, the reaction mixture was filtered to obtain solid products. Then, the solid products were washed out with water, thereby obtaining 2.4 g (yield: 90percent) of Intermediate I-3-1
90% for 5 h; 2-(phenylamino)benzoic acid (2.5 grams (g), 0.12 moles (mol)), thionyl chloride (1.39 g, 0.13 mol), and 50 milliliters (mL) of methanol were added to a flask, and the mixture was allowed to react for 5 hours. Once the reaction was completed, the reaction mixture was filtered, and the remaining solid was washed with water to obtain Intermediate I-3-1 (2.4 g, 90percent).
81%
Stage #1: at 0℃; for 0.166667 h; Inert atmosphere
Stage #2: at 90℃;
In N2in the gas purification system, mixing and stirring N-phenyl-O-aminobenzoic acid (46.9mmol) and methanol solvent. The mixture at 0 °C restiring at a temperature of 10 minutes, and is slow to instillment thionyl chloride (21.2mmol). In the mixed solution is 90 °C temperature stirring 12 hours or more. After the completion of reaction, to remove the solvent, and distilled water and for the mixed solution is then extracted with ethyl acetate. From the extraction of using magnesium sulphate remove the moisture in the organic layer, and removing the solvent. The material through the use of hexane and ethyl acetate to carry out wet refining column chromatography, thereby obtaining compound crocatus of the liquid is "b". (Yield: 81percent)
80% at 0 - 90℃; Inert atmosphere Compound 1A(4.52 g, 21.2 mmol) was mixed with a methanol solvent(100ml) and then stirred under a nitrogen atmosphere. After further stirring at 0° C. for 10 minutes, 1 equivalent of thionyl chloride (21.2 mmol) was slowly added dropwise. The mixed solution was stirred at 90° C. for 12 hours or longer. After completion of the reaction, the solvent was removed, and distilled water and ethyl acetate were added to extract an organic layer. The moisture remaining in the extracted organic layer was removed using magnesium sulfate, followed by removal of the solvent, and then a crude product was subjected to wet purification using column chromatography using hexane and ethyl acetate to obtain a dark yellow liquid 1B(3.84 g, yield 80percent).

Reference: [1] Patent: WO2011/93609, 2011, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2012/39561, 2012, A1, . Location in patent: Page/Page column 23
[3] Patent: WO2013/45411, 2013, A1, . Location in patent: Paragraph 0097
[4] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081
[5] Patent: US2017/5275, 2017, A1, . Location in patent: Paragraph 0283; 0284; 0285
[6] Patent: US2017/25620, 2017, A1, . Location in patent: Paragraph 0324; 0325; 0326
[7] Archiv der Pharmazie, 1984, vol. 317, # 7, p. 595 - 606
[8] Patent: CN105585577, 2016, A, . Location in patent: Paragraph 0101; 0102; 0103; 0104
[9] Patent: US2018/166636, 2018, A1, . Location in patent: Paragraph 0109; 0110
[10] Journal of the American Chemical Society, 1935, vol. 57, p. 195,196
[11] Journal of the American Chemical Society, 1933, vol. 55, p. 4294,4297, 4298
[12] Helvetica Chimica Acta, 1944, vol. 27, p. 616,617
[13] Journal of Materials Chemistry, 2007, vol. 17, # 12, p. 1209 - 1215
[14] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1971 - 1985
  • 8
  • [ 108-86-1 ]
  • [ 134-20-3 ]
  • [ 35708-19-1 ]
YieldReaction ConditionsOperation in experiment
93% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In tolueneInert atmosphere; Reflux 15 g of methyl-2-aminobenzoate,15.6 grams of bromobenzene,0.9 g of Pd2 (dba) 3,0.4 g of P (t-Bu) 3 and 28.6 g of Na (t-BuO) were placed in a round bottom three-necked flask under a nitrogen atmosphere,Add 100 ml of toluene,The mixture was stirred and refluxed.After completion of the reaction,The resulting solution was washed with dichloromethane and water. Collecting organic layer,Dried over MgSO4 and separated by column to give methyl-2- (phenylamino) benzoate (21.0 g, 93percent yield).
65% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 12 h; Reflux A solution of 85 g (541.37 mmol) of bromobenzene, 98.2 g (649.64 mmol) of methyl 2-aminobenzoate, 78.0 g (812.05 mmol) of sodium tert-butoxide and tris (dibenzylideneacetone) dipalladium g (10.83 mmmol) was suspended in 1803 ml of toluene,Tert-butylphosphine10.3 mL (43.31 mmol) were added thereto, followed by reflux stirring for 12 hours. Extracted with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v) to obtain 80.0 g (yield: 65percent) of the intermediate product (A)
Reference: [1] Tetrahedron, 2006, vol. 62, # 48, p. 11100 - 11105
[2] Patent: TWI579270, 2017, B, . Location in patent: Paragraph 0094; 0095
[3] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646
[4] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8107 - 8109
[5] Patent: KR2016/102142, 2016, A, . Location in patent: Paragraph 0215; 0218; 0219
  • 9
  • [ 91-40-7 ]
  • [ 77-78-1 ]
  • [ 35708-19-1 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In acetone for 2 h; Reflux To a flask charged with N-phenyl-anthranilic acid (10.0 g, 46.9 mmol) and potassium carbonate (6.48 g, 46.9 mmol) in acetone (140 mL) was added dimethyl sulfate (7.56 mL, 79.7 mmol) at room temperature. The flask was attached to a reflux condenser and heated to reflux. After 2 h, the was cooled to rt, and poured onto 10 crushed ice. The resulting mixture was extracted with dichloromethane and then dried over Na2S04. The resulting solution was filtered and concentrated. The resulting residue was purified via silica gel chromatography, eluted with hexane:ethyl acetate = 6:4, to afford the product as a yellow oil in 94percent yield.
92% With potassium carbonate In acetone for 2 h; Reflux Commercially available N-phenyl anthranilic acid (1) (2.0 g, 10 mmol) in acetone (30 mL) was refluxed with dimethyl sulphate (2.0 gr, 1.55 mL, 15 mmol) and potassium carbonate (1.38 g, 10 mmol) for 2 hrs. The progress of the reaction was monitored by TLC and when reaction was judged complete, the reaction mixture was allowed to cool to room temperature and poured into crushed ice. The aqueous layer was extracted with CH2C12 (2 x 30mL), dried over anhydrous MgS04, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with gradient elution (10 to 40percent EtOAc-hexane) to afford the title compound as light yellow oil (2.1 g, 92percent yield). 1H NMR (300 MHz, DMSO- 6): δ 9.29 (s, 1H), 7.88 (d, 1H, J = 7.8 Hz), 7.45-7.30 (m, 3H), 7.28-7.18 (m, 3H), 7.07 (t, 1H, J = 7.5 Hz), 6.80 (t, 1H, J = 7.5 Hz), 3.85 (s, 3H). LCMS (ESI) m/z 228 (MH+).
Reference: [1] Patent: KR2018/30860, 2018, A, . Location in patent: Paragraph 0043-0045
[2] Patent: WO2014/165307, 2014, A2, . Location in patent: Paragraph 0314
[3] Journal of the American Chemical Society, 1935, vol. 57, p. 195,196
  • 10
  • [ 591-50-4 ]
  • [ 134-20-3 ]
  • [ 35708-19-1 ]
Reference: [1] Chemische Berichte, 1986, vol. 119, # 10, p. 3165 - 3197
[2] Chemistry - An Asian Journal, 2015, vol. 10, # 6, p. 1402 - 1409
[3] Chemical Communications, 2016, vol. 52, # 52, p. 8149 - 8151
[4] Tetrahedron Letters, 2001, vol. 42, # 29, p. 4791 - 4793
[5] Chemische Berichte, 1980, vol. 113, # 1, p. 358 - 384
[6] Journal of Materials Chemistry C, 2016, vol. 4, # 33, p. 7869 - 7874
  • 11
  • [ 62-53-3 ]
  • [ 278175-48-7 ]
  • [ 35708-19-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9563 - 9573
  • 12
  • [ 610-94-6 ]
  • [ 62-53-3 ]
  • [ 35708-19-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 7, p. 2531 - 2535[2] Angew. Chem., 2016, vol. 128, # 7, p. 2577 - 2581,5
[3] Patent: US2009/131527, 2009, A1, . Location in patent: Page/Page column 6
[4] Journal of Organic Chemistry, 2014, vol. 79, # 3, p. 955 - 962
  • 13
  • [ 134-20-3 ]
  • [ 98-80-6 ]
  • [ 35708-19-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 10, p. 2897 - 2901
  • 14
  • [ 591-50-4 ]
  • [ 12775-96-1 ]
  • [ 134-20-3 ]
  • [ 35708-19-1 ]
Reference: [1] Patent: US6235730, 2001, B1,
  • 15
  • [ 119-36-8 ]
  • [ 35708-19-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9563 - 9573
  • 16
  • [ 117560-06-2 ]
  • [ 134-20-3 ]
  • [ 35708-19-1 ]
  • [ 160246-88-8 ]
  • [ 572874-62-5 ]
Reference: [1] Molecules, 2005, vol. 10, # 1, p. 226 - 237
  • 17
  • [ 91-40-7 ]
  • [ 74-88-4 ]
  • [ 35708-19-1 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 583 - 588
  • 18
  • [ 67-56-1 ]
  • [ 19263-30-0 ]
  • [ 35708-19-1 ]
Reference: [1] Chemische Berichte, 1968, vol. 101, # 9, p. 3079 - 3088
  • 19
  • [ 35708-19-1 ]
  • [ 1333316-35-0 ]
Reference: [1] Patent: WO2014/165307, 2014, A2,
[2] Patent: US2018/166636, 2018, A1,
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