Home Cart 0 Sign in  

[ CAS No. 75844-40-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 75844-40-5
Chemical Structure| 75844-40-5
Structure of 75844-40-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 75844-40-5 ]

Related Doc. of [ 75844-40-5 ]

SDS
Alternatived Products of [ 75844-40-5 ]
Alternatived Products of [ 75844-40-5 ]

Product Details of [ 75844-40-5 ]

CAS No. :75844-40-5MDL No. :MFCD00089490
Formula : C9H8N2O Boiling Point : 311.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :160.17Pubchem ID :135452533
Synonyms :

Computed Properties of [ 75844-40-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 75844-40-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 75844-40-5 ]

  • Upstream synthesis route of [ 75844-40-5 ]
  • Downstream synthetic route of [ 75844-40-5 ]

[ 75844-40-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 39549-79-6 ]
  • [ 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
  • [ 1829-21-6 ]
  • [ 6313-33-3 ]
  • [ 75844-40-5 ]
YieldReaction ConditionsOperation in experiment
82% With copper 8-hydroxyquinolinate; sodium hydroxide In water at 100℃; for 0.5 h; Microwave irradiation 1 mmol of 2-iodo-4-methylbenzoic acid was added to the reaction vessel, 1 mmol of formamidine hydrochloride, 0.05 mmol of 8-quinolinol copper (B), 1 mmol of sodium hydroxide and 3 mL of water. Into the microwave reaction The reactor was then heated in a microwave reactor at 150 W for 100 ° C to 30 minutes and cooled to room temperature. And extracted with ethyl acetate The product was removed and concentrated under reduced pressure. The product was purified by column chromatography to give a white solid in 82percent yield.
Reference: [1] Patent: CN103864702, 2016, B, . Location in patent: Paragraph 0056
  • 3
  • [ 64-18-6 ]
  • [ 39549-79-6 ]
  • [ 75844-40-5 ]
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
  • 4
  • [ 77287-34-4 ]
  • [ 2305-36-4 ]
  • [ 75844-40-5 ]
YieldReaction ConditionsOperation in experiment
82% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2794 - 2809
[3] Journal fuer Praktische Chemie (Leipzig), 1895, vol. &lt;2&gt; 51, p. 566
[4] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[5] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 70
[6] Chemistry and Biodiversity, 2018, vol. 15, # 6,
  • 5
  • [ 67-56-1 ]
  • [ 39549-79-6 ]
  • [ 75844-40-5 ]
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
  • 6
  • [ 39549-79-6 ]
  • [ 144-62-7 ]
  • [ 75844-40-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 7
  • [ 39549-79-6 ]
  • [ 122-51-0 ]
  • [ 75844-40-5 ]
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
  • 8
  • [ 26830-95-5 ]
  • [ 75844-40-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 12
[2] Journal of the American Chemical Society, 1905, vol. 27, p. 1301
  • 9
  • [ 26830-96-6 ]
  • [ 75844-40-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. &lt;2&gt; 40, p. 12
[2] Patent: WO2013/100632, 2013, A1,
[3] Patent: US2014/371219, 2014, A1,
  • 10
  • [ 27329-27-7 ]
  • [ 75844-40-5 ]
Reference: [1] Patent: US2013/210844, 2013, A1,
  • 11
  • [ 65078-05-9 ]
  • [ 75844-40-5 ]
Reference: [1] Patent: US2013/210844, 2013, A1,
  • 12
  • [ 50424-81-2 ]
  • [ 75844-40-5 ]
Reference: [1] Patent: US2013/210844, 2013, A1,
  • 13
  • [ 64-18-6 ]
  • [ 26830-96-6 ]
  • [ 75844-40-5 ]
Reference: [1] Journal of the American Chemical Society, 1905, vol. 27, p. 1301
  • 14
  • [ 75844-40-5 ]
  • [ 90272-83-6 ]
Reference: [1] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 70
Historical Records

Related Functional Groups of
[ 75844-40-5 ]

Amides

Chemical Structure| 17329-31-6

[ 17329-31-6 ]

6-Aminoquinazolin-4(3H)-one

Similarity: 0.98

Chemical Structure| 19181-54-5

[ 19181-54-5 ]

8-Methylquinazolin-4(3H)-one

Similarity: 0.97

Chemical Structure| 117297-41-3

[ 117297-41-3 ]

4-oxo-3,4-Dihydroquinazoline-6-carbonitrile

Similarity: 0.93

Chemical Structure| 202197-73-7

[ 202197-73-7 ]

4-Oxo-3,4-dihydroquinazoline-7-carboxylic acid

Similarity: 0.86

Chemical Structure| 109229-22-3

[ 109229-22-3 ]

6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

Similarity: 0.86

Related Parent Nucleus of
[ 75844-40-5 ]

Quinazolines

Chemical Structure| 17329-31-6

[ 17329-31-6 ]

6-Aminoquinazolin-4(3H)-one

Similarity: 0.98

Chemical Structure| 19181-54-5

[ 19181-54-5 ]

8-Methylquinazolin-4(3H)-one

Similarity: 0.97

Chemical Structure| 117297-41-3

[ 117297-41-3 ]

4-oxo-3,4-Dihydroquinazoline-6-carbonitrile

Similarity: 0.93

Chemical Structure| 202197-73-7

[ 202197-73-7 ]

4-Oxo-3,4-dihydroquinazoline-7-carboxylic acid

Similarity: 0.86

Chemical Structure| 194851-16-6

[ 194851-16-6 ]

7-Bromoquinazolin-4(3H)-one

Similarity: 0.85