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[ CAS No. 39549-79-6 ]

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Chemical Structure| 39549-79-6
Chemical Structure| 39549-79-6
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CAS No. :39549-79-6 MDL No. :MFCD00221474
Formula : C8H10N2O Boiling Point : 282.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :150.18 g/mol Pubchem ID :2801474
Synonyms :

Safety of [ 39549-79-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 39549-79-6 ]

  • Upstream synthesis route of [ 39549-79-6 ]
  • Downstream synthetic route of [ 39549-79-6 ]

[ 39549-79-6 ] Synthesis Path-Upstream   1~19

  • 1
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  • [ 77287-34-4 ]
  • [ 75844-40-5 ]
YieldReaction ConditionsOperation in experiment
76% With ytterbium(III) triflate In 1,3,5-trimethyl-benzene at 165℃; for 6 h; Inert atmosphere General procedure: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 molpercent), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100percent. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.
Reference: [1] Heterocycles, 2015, vol. 90, # 2, p. 857 - 865
  • 2
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YieldReaction ConditionsOperation in experiment
91% at 100℃; for 6 h; 2-amino-4-mthylbenzamide (4.93 g, 32.8 mmol) obtained in above was added with formic acid (30 mL, 787.9 mmol), followed by stirring for 6 hours at 100°C. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and washed with water. The filtered solid was dried with warm wind in an oven (40°C) for 6 hours or more to obtain the title compound (4.79 g, 91percent). 1H-NMR Spectrum (300 MHz, DMSO-rftf): δ 8.06 (s, 1H), 8.00 (d, 1H), 7.47 (s, 1H), 7.34 (d, 1H), 2.45 (s, 3H) MS(ESI+, m/z): 161 [M+H]+
91% at 100℃; for 6 h; 2-amino-4-methylbenzamide (4.93 g, 32.8 mmol) obtained in <Step 1> above was added with formic acid (30 mL, 787.9 mmol), followed by stirring for 6 hours at 100° C. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and washed with water. The filtered solid was dried with warm wind in an oven (40° C.) for 6 hours or more to obtain the title compound (4.79 g, 91percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.06 (s, 1H), 8.00 (d, 1H), 7.47 (s, 1H), 7.34 (d, 1H), 2.45 (s, 3H) MS (ESI+, m/z): 161 [M+H]+
84% at 100℃; for 6 h; A mixture of 2-amino-4-methylbenzamide (20 g, 133 mmol) and formic acid (120 ml, 3129 mmol) was heated to 100 0C for 6 h. The reaction was cooled to RT and the volatiles were removed under reduced pressure. The residue was then washed carefully with aqueous saturated sodium bicarbonate and then with water. The tan solid was then dried in a vacuum oven at 45 0C overnight to give 7-methylquinazolin-4(3H)-one (18.00 g, 84percent yield). MS (ESI, pos. ion) m/z: 161 [M+H]+
Reference: [1] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 50
[2] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0344; 0345; 0346
[3] Patent: WO2008/153947, 2008, A2, . Location in patent: Page/Page column 43; 58
[4] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 12
[5] Patent: WO2007/76092, 2007, A2, . Location in patent: Page/Page column 115-116
  • 3
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YieldReaction ConditionsOperation in experiment
87% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-amino-4-methylbenzamide (75 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent,Then, column chromatography (developing solvent: petroleum ether / ethyl acetate)The pure target compound was obtained in a yield of 87percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0040; 0041; 0042; 0043
  • 4
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  • [ 144-62-7 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 5
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  • [ 122-51-0 ]
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YieldReaction ConditionsOperation in experiment
1.1 g at 110℃; for 4 h; Sealed tube A suspension of 2-amino-4-methylbenzamide (1.2 g, 8.0 mmol) in CH(OEt)3 (10 mL) was heated in a sealed tube at 110° C. for 4 h.
Then the reaction was quenched with aq. NaHCO3 solution at rt and the precipitate obtained was filtered and dried.
The solid mass was purified by column chromatography to afford 1.1 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 12.14 (br s, 1H), 8.05 (s, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.47 (s, 1H), 7.34 (d, J=7.8 Hz, 1H), 2.45 (s, 3H).
Reference: [1] Patent: US2013/210844, 2013, A1, . Location in patent: Paragraph 0438; 0439
  • 6
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  • [ 25171-19-1 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 1759,1765
  • 7
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Reference: [1] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
[2] Journal of the Chemical Society, 1929, p. 2557
[3] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
  • 8
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  • [ 2305-36-4 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 1539[2] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 15
  • 9
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YieldReaction ConditionsOperation in experiment
53% With sulfuric acid In water at 120℃; for 0.333333 h; Concentrated sulfuric acid (3 mL) was carefully added to a suspension of 2- amino-4-methylbenzonitrile (800 mg, 6.1 mmol) in H2O (1 mL). The solution was then placed into an oil bath, pre-heated to 120 0C, the reaction stirred for 20 min and then immediately cooled in an ice bath. The solution was made basic via the addition of 5 percent NaOH and the resulting solid collected via vacuum filtration. 484.4 mg (53 percent) of the title compound as a light brown solid were obtained. 1H NMR (DMSO-dβ) δ 7.63 (br s, 1 H), 7.42 (d, 1 H), 6.95 (br s, 1 H), 6.55 (br s, 2 H), 6.45 - 6.48 (m, 1 H), 6.29 (ddd, 1 H), 2.16 (s, 3 H). MS (ES) 134 (M - 16).
43% With potassium hydroxide In ethanol for 8 h; Reflux 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO- 6): δ 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, lH), 2.14 (s, 3H)
43% With potassium hydroxide In ethanol for 8 h; Reflux 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, 1H), 2.14 (s, 3H)
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 47, p. 15786 - 15787
[2] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 382 - 385
[3] Patent: WO2006/74223, 2006, A2, . Location in patent: Page/Page column 51
[4] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 49; 50
[5] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0342; 0343
[6] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 12
  • 10
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 3 h; Inert atmosphere
Stage #2: With ammonium hydroxide In water; N,N-dimethyl-formamide for 16 h;
Compound 22 (3.00 g, 19.8 mmol) in dry DMF (100 mL) under Ar was treated with EDC.HCl (4.17 g, 21.8 mmol) and HOBt (3.33 g, 21.8 mmol) for 3 h, after which aq. NH3 (35percent, 20 mL) was added and the mixture was stirred for 16 h. The evaporation residue, in EtOAc, was washed twice with water and with brine. Drying and evaporation gave 25 (2.04 g, 69percent) as an off-white solid: mp 151-153 °C (lit. [62]
mp 148 °C); 1H NMR ((CD3)2SO) δ 2.22 (3 H, s, Me), 6.35 (1 H, dd, J = 8.0, 1.2, 5-H), 6.52 (1 H, d, J = 0.5 Hz, 3-H), 6.57 (2 H, s, NH2), 6.95 (1 H, brs, CONHH), 7.48 (1 H, d, J = 8.0 Hz, 6-H), 7.65 (1 H, brs, CONHH); 13C NMR ((CD3)2SO) (HSQC/HMBC) δ 21.03 (Me), 111.14 (1-C), 115.61 (5-C), 116.44 (3-C), 128.77 (6-C), 141.55 (2-C), 150.31 (4-C), 171.19 (C=O).
64% With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1 h; To a stirred solution of 2-amino-4-methyl-benzoic acid (300 mg, 1.99 mmol) in THF (6 mL),EDC.HCl (569 mg, 2.98 mmol), HOBt·NH3 (447 mg, 2.98 mmol) and DIPEA (1.06 mL, 5.96mmol) were added at RT and stirred for 1 h (TLC indicated complete consumption of startingmaterial). The reaction mixture was diluted with water (30 mL), extracted with EtOAc (3 x25 mL). The combined organic extracts were dried over Na2S04, concentrated under reducedpressure to give the crude compound which was purified by flash column chromatography(100-200 silica gel, 5 g, 50percent EtOAc-Hexane) to afford 2-amino-4-methyl-benzamide (190mg, 64percent) as a white solid 1H NMR [300 MHz, DMSO-d6]: J 7.62 (brs, 1H), 7.42 (d, J = 8.1 Hz, 1H), 6.93 (brs, 1H),6.54-6.46 (m, 3H), 6.30- 6.27 (m, 1H), 2.15 (s, 3H).
60% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; N,N-dimethyl-formamide at 20℃; for 24 h; Inert atmosphere Accordingtoaliteratureprocedure,3toasolutionof2-amino-3-methylbenzoicacid(151mg,1.00mmol,1.0eq)indegassedDMF(2.00mL)wereaddedHOBt(162mg,1.20mmol,1.2eq.),EDCI.HCl(230mg,1.20mmol,1.2eq.),N,N-diisopropylethylamine(350μL,2.00mmol,2.0eq),and7MNH3/MeOH(429μL,1.50mmol,1.5eq.).Thesolutionwasstirredatroomtemperaturefor24hoursthenpouredoverwaterandtheaqueouslayerextractedwithEtOAc(320mL),thecombinedorganiclayerswashedwithbrine(25mL),driedwithNa2SO4andconcentratedinvacuo.TheresiduewaspurifiedbyFCC(gradient50percentEtOAc/hexanes to 80percent EtOAc/hexanes) to give 2-amino-3-methylbenzamide (90.0 mg,0.599mmol,60percent)asawhiteamorphoussolid;mp:144–146°C,lit.144–145°C.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 118, p. 316 - 327
[2] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 53; 54
[3] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
  • 11
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 602 - 604
[2] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 12
  • 12
  • [ 65078-05-9 ]
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YieldReaction ConditionsOperation in experiment
1.2 g With iron; ammonium chloride In ethanol; water for 2 h; Reflux General procedure: To a solution of 5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine (1.0 g, 3.0 mmol) in a mixture of EtOH:H2O (8:2, 10 mL) were added iron powder (1.26 g, 4.8 mmol), and NH4Cl (1.6 g, 30.0 mmol).
The reaction mass was heated at reflux for 2 h and filtered.
The filtrate was concentrated and the residue was purified by column chromatography to afford 0.800 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.18 (s, 1H), 8.35 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.42-7.24 (m, 3H), 6.86 (d, J=7.5 Hz, 1H), 5.84 (s, 2H). The title compound was prepared following the procedure described in Step 3 of Intermediate-i using 4-methyl- 2-nitrobenzamide (1.60 g, 8.88 mmol), iron powder (2.97 g,53.33 mmol), and NH4C1 (2.85 g, 53.33 mmol) in EtOH (8 mE) and water (2 mE) to afford 1.2 g of the title product. 1HNMR (300 MHz, DMSO-d5): ö 7.62 (br s, 1H), 7.42 (d, J=7.8 Hz, 1H), 6.93 (br s, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.29 (d, J=7.8 Hz, 1H), 2.15 (s, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 549 - 551
[2] Patent: US2013/210844, 2013, A1, . Location in patent: Paragraph 0263; 0269; 0436; 0437
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Reference: [1] Molecules, 2018, vol. 23, # 11,
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Reference: [1] Arkivoc, 2012, vol. 2012, # 8, p. 198 - 213
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 549 - 551
[2] Patent: US2013/210844, 2013, A1,
[3] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
  • 16
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Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3311 - 3316
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Reference: [1] Patent: US2013/210844, 2013, A1,
  • 18
  • [ 26830-95-5 ]
  • [ 39549-79-6 ]
  • [ 26830-96-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
[2] Journal of the Chemical Society, 1929, p. 2557
[3] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
  • 19
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Reference: [1] Journal of the Chemical Society, 1929, p. 2557
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