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[ CAS No. 762-42-5 ]

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Chemical Structure| 762-42-5
Chemical Structure| 762-42-5
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Product Details of [ 762-42-5 ]

CAS No. :762-42-5 MDL No. :MFCD00008456
Formula : C6H6O4 Boiling Point : 204.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :142.11 g/mol Pubchem ID :12980
Synonyms :

Safety of [ 762-42-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:1760
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 762-42-5 ]

  • Upstream synthesis route of [ 762-42-5 ]
  • Downstream synthetic route of [ 762-42-5 ]

[ 762-42-5 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 135641-60-0 ]
  • [ 762-42-5 ]
  • [ 15366-34-4 ]
  • [ 135641-61-1 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 7, p. 1701 - 1757
  • 2
  • [ 762-42-5 ]
  • [ 5416-80-8 ]
  • [ 113002-23-6 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 27, p. 3079 - 3082
  • 3
  • [ 762-42-5 ]
  • [ 164254-26-6 ]
  • [ 73406-50-5 ]
  • [ 164254-30-2 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 18, p. 5347 - 5357
  • 4
  • [ 762-42-5 ]
  • [ 2450-71-7 ]
  • [ 605-38-9 ]
YieldReaction ConditionsOperation in experiment
93% With dipotassium peroxodisulfate; silver trifluoromethanesulfonate In toluene at 80℃; for 6 h; Sealed tube A mixture of propargylamine (1a, 1.0 mmol, 55.1 mg), dimethyl acetylenedicarboxylate (2a, 1.3 mmol, 185.0 mg), AgOTf (25.7 mg, 0.1 mmol) and K2S2O8 (270.0 mg, 1.0 mmol) in toluene (20 mL) in a thick-walled screw-capped Pyrex tube was stirred with a magnetic stirrer at 80 °C for 6 h. After removal of the solvent under reduced pressure, purification was performed by flash column chromatography on silica gel with petroleum ether/ethyl acetate (8:2) as eluent to afford 3aa in 93 percent yield (181.3 mg, 0.93 mmol).
Reference: [1] Tetrahedron, 2017, vol. 73, # 42, p. 6080 - 6084
  • 5
  • [ 762-42-5 ]
  • [ 3449-48-7 ]
  • [ 1293289-06-1 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 14, p. 1649 - 1652
[2] Tetrahedron Letters, 2011, vol. 52, # 14, p. 1649 - 1652
  • 6
  • [ 62-53-3 ]
  • [ 762-42-5 ]
  • [ 5965-59-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767
  • 7
  • [ 41609-04-5 ]
  • [ 762-42-5 ]
  • [ 108-44-1 ]
  • [ 5220-49-5 ]
YieldReaction ConditionsOperation in experiment
55% With tert.-butylhydroperoxide; copper diacetate In water at 30℃; for 12 h; General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), aryl or alkyl amine (1.0 mmol), Cu(OAc)2 (8 molpercent) and TBHP (4.0 mmol, 0.56 mL of a 70percent aqueous solution) in water (0.5 mL) was stirred at 30 °C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/ petroleum ether (60-80 °C)].
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 32, p. 3069 - 3076
  • 8
  • [ 127-07-1 ]
  • [ 762-42-5 ]
  • [ 10068-07-2 ]
Reference: [1] Synthesis, 1985, vol. NO. 12, p. 1100 - 1164
[2] Liebigs Annalen der Chemie, 1982, vol. No. 4, p. 817 - 820
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 812 - 823
  • 9
  • [ 762-42-5 ]
  • [ 10068-07-2 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 28, p. 6304 - 6312
[2] RSC Advances, 2018, vol. 8, # 13, p. 7080 - 7088
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6329 - 6343
  • 10
  • [ 127-07-1 ]
  • [ 762-42-5 ]
  • [ 10068-07-2 ]
Reference: [1] Patent: US6200975, 2001, B1,
  • 11
  • [ 127-07-1 ]
  • [ 762-42-5 ]
  • [ 77094-88-3 ]
  • [ 77094-89-4 ]
  • [ 10068-07-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 9-10, p. 478 - 480
[2] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 9-10, p. 478 - 480
  • 12
  • [ 613-92-3 ]
  • [ 762-42-5 ]
  • [ 62222-38-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 22, p. 5336 - 5339
  • 13
  • [ 762-42-5 ]
  • [ 55781-86-7 ]
Reference: [1] Patent: EP2530078, 2012, A1,
  • 14
  • [ 762-42-5 ]
  • [ 60-34-4 ]
  • [ 51985-95-6 ]
Reference: [1] Patent: US5405829, 1995, A,
[2] Patent: US5580986, 1996, A,
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8174 - 8187
[4] Patent: WO2012/122340, 2012, A1, . Location in patent: Page/Page column 69
  • 15
  • [ 762-42-5 ]
  • [ 51985-95-6 ]
Reference: [1] Patent: WO2010/127975, 2010, A1,
  • 16
  • [ 302-15-8 ]
  • [ 762-42-5 ]
  • [ 52867-42-2 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With triethylamine In methanol; water at 20℃; for 0.5 h;
Stage #2: at 70℃; for 18 h;
Step l:Methyl 3-hydroxy-l-methyl-lH-pyrazole-5-carboxylate (3_41_2) [00351] Triethylamine (66 mL, 474.4 mmol) was added to a solution of methylhydrazine sulfuric acid salt (30.4 g, 211 mmol) in water (150 mL) and methanol (300 mL) at room temperature. The mixture was stirred for 0.5 hour at room temperature, but-2-ynedioic acid dimethyl ester (30 g, 211 mmol) was added and the mixture was stirred for 18 hours at 70°C. The reaction mixture was kept at room temperature for two days and the solid was collected by filtration and dried to give 12 g of the desired compound. The filtrate was concentrated, treated with ice and the solid was collected by filtration, and dried to give an additional 5 g of the desired compound 3_41_2 (17 g, 52 percent yield) as a yellow solid. [00352] NMR (400 MHz, DMSO-c: δ = 3.79 (s, 3H), 3.88 (s, 3H), 6.01 (s, 1H), 10.05 (s, 1H).
16.6%
Stage #1: With triethylamine In methanol; water at 20℃; for 0.5 h;
Stage #2: at 70℃; for 18 h;
TEA (44.2 mL, 316.7 mmol) was added to a solution of methylhydrazine sulfate (20.3 g, 140.7 mmol) in H2O (100 mL) and MeOH (200 mL) at room temperature, and the mixture was stirred for 0.5 h at rt.
Dimethyl but-2-ynedioate (20 g, 140.7 mmol) was added to the mixture, the mixture was stirred for 18 h at 70° C., followed by stirring at rt for 36 h.
The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give the product as a white solid (3.65 g, 16.6percent yield).
Reference: [1] Patent: WO2013/110643, 2013, A1, . Location in patent: Paragraph 00351; 00352
[2] Patent: US2018/170909, 2018, A1, . Location in patent: Paragraph 1891; 1892
[3] Patent: WO2015/50989, 2015, A2, . Location in patent: Paragraph 00299; 00300
  • 17
  • [ 762-42-5 ]
  • [ 52867-42-2 ]
YieldReaction ConditionsOperation in experiment
60% With methylhydrazine sulfuric acid; triethylamine In methanol for 15 h; Reflux The lOOmmol methyl hydrazine sulfate was added to a three-necked round-bottomed flask, dissolved with 200mL of methanol, followed by addition of 200mmol triethylamine free, finally adding lOOmmol dimethyl butynoate, heated to 60 ° C, magnetic stirring, refluxed 15h ;After the reaction is complete, stop heating, cooled to 5 ° C, allowed to stand for 2 days, until the white crystals precipitated, filtered, washed with ethanol, and dried to obtain methyl 3-hydroxy-1-methylpyrazole-5-carboxylate Rate of 60percent, purity 95percent
Reference: [1] Patent: CN105175335, 2017, B, . Location in patent: Paragraph 0029; 0043-0045
[2] Patent: WO2010/127975, 2010, A1,
  • 18
  • [ 762-42-5 ]
  • [ 52867-42-2 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With triethylamine In methanol; water at 20℃; for 0.5 h;
Stage #2: at 70℃; for 22 h;
Et3N (17.3 mL, 0.12 mol) was added to a solution of dimethyl but-2-ynedioate (8 g, 0.05mmol) in MeOH (80 mL), H20 (40 mL) and stirred at RT for 30 min. Methyl hydrazinesulfate (8.92 g, 61.9 mol) was added and the reaction mixture was stirred at 70 °C for 22 h.The solution was allowed to stand at R T overnight and the solid formed was filtered, driedunder high vacuum to afford methyl5-hydroxy-2-methyl-pyrazole-3-carboxylate (3.5 g,40percent) as a pale brown solid.LCMS: m/z: 157.3 [M+Ht.
Reference: [1] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 117
  • 19
  • [ 762-42-5 ]
  • [ 60-34-4 ]
  • [ 52867-42-2 ]
YieldReaction ConditionsOperation in experiment
23% at 70℃; To a solution of dimethyl acetylenedicarboxylate (5 g, 35.18 mmol) in methanol (25 mL)-water (2.5mL) was added dropwise methylhydrazine (1.945 g, 42.22 mmol) at room temperature. The reaction mixture was stirred at 70°C overnight, cooled to room temperature, concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (90:10-3:4)] to give the title compound (1.26 g) as a colorless oil (yield 23percent). MS (ESI+): [M+H]+157. 1H NMR (300 MHz, DMSO-d6) δ 3.79 (3H, s), 3.88 (3H, s), 6.00 (1H, s), 10.06 (1H, s).
5 g at 0 - 70℃; for 10 h; The compound methyl hydrazine (10g) was dissolved in methanol (20mL) and water (10mL), cooled to 0 degree, stirred for 15min, then compound 21 (12g) was added dropwise to the reaction system, heated to 70 degrees for 10h, then the system temperature was returned to room temperature, the reaction 12h, filtered off with suction, the filter cake was washed with water (5mL), dried to give 22 as a pale yellow solid 5g
5 g at 0 - 70℃; for 10.25 h; The compound methyl hydrazine (10 g) was dissolved in methanol (20 mL) and water (10 mL).The temperature was lowered to 0 °, stirred for 15 min, and then Compound 21 (12 g) was added dropwise to the reaction system.Heat to 70 ° for 10 h, then return the system temperature to room temperature.After 12 h of reaction, suction filtration, and the filter cake was washed with water (5 mL).Get 22 pale yellow solids 5g
Reference: [1] Patent: EP2530078, 2012, A1, . Location in patent: Page/Page column 208-209
[2] Chemische Berichte, 1988, vol. 121, p. 2007 - 2012
[3] Patent: CN108250122, 2018, A, . Location in patent: Paragraph 0312-0316
[4] Patent: CN108264520, 2018, A, . Location in patent: Paragraph 0193; 0194; 0195; 0196; 0197
  • 20
  • [ 563-79-1 ]
  • [ 762-42-5 ]
  • [ 72163-16-7 ]
  • [ 72163-25-8 ]
  • [ 5331-33-9 ]
  • [ 28868-76-0 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, p. 288 - 301
  • 21
  • [ 563-79-1 ]
  • [ 762-42-5 ]
  • [ 72163-16-7 ]
  • [ 72163-26-9 ]
  • [ 72163-23-6 ]
  • [ 28868-76-0 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, p. 288 - 301
  • 22
  • [ 116273-92-8 ]
  • [ 762-42-5 ]
  • [ 60705-25-1 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 48, p. 13857 - 13864
  • 23
  • [ 496-64-0 ]
  • [ 762-42-5 ]
  • [ 36669-02-0 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1347 - 1356
  • 24
  • [ 75232-81-4 ]
  • [ 762-42-5 ]
  • [ 36669-02-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4810 - 4812
  • 25
  • [ 102308-33-8 ]
  • [ 762-42-5 ]
  • [ 66323-03-3 ]
  • [ 82217-53-6 ]
Reference: [1] Tetrahedron, 1981, vol. 37, # 23, p. 4081 - 4086
  • 26
  • [ 31411-71-9 ]
  • [ 762-42-5 ]
  • [ 66323-03-3 ]
Reference: [1] Chemistry Letters, 1978, p. 649 - 652
  • 27
  • [ 54125-02-9 ]
  • [ 762-42-5 ]
  • [ 22479-95-4 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Journal of the American Chemical Society, 1974, vol. 96, p. 7807 - 7808
[3] Journal of the American Chemical Society, 1979, vol. 101, p. 6996 - 7000
[4] Synthetic Communications, 1991, vol. 21, # 8-9, p. 1055 - 1069
  • 28
  • [ 762-42-5 ]
  • [ 22479-95-4 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 4, p. 1487 - 1489
  • 29
  • [ 59414-23-2 ]
  • [ 762-42-5 ]
  • [ 22479-95-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 7, p. 1832 - 1835
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 7, p. 1832 - 1835
  • 30
  • [ 762-42-5 ]
  • [ 74586-53-1 ]
Reference: [1] Patent: US5270309, 1993, A,
  • 31
  • [ 66064-57-1 ]
  • [ 762-42-5 ]
  • [ 112110-16-4 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 33, p. 10047 - 10054
  • 32
  • [ 16713-45-4 ]
  • [ 762-42-5 ]
  • [ 112110-16-4 ]
Reference: [1] Liebigs Annales, 1996, # 5, p. 739 - 741
  • 33
  • [ 118493-85-9 ]
  • [ 762-42-5 ]
  • [ 878158-18-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 23, p. 6646 - 6649
  • 34
  • [ 518047-98-8 ]
  • [ 762-42-5 ]
  • [ 519032-08-7 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: at 20℃; for 2 h;
Stage #2: With xylene In methanol at 90 - 120℃; for 16 h; Inert atmosphere
Benzyl 2-amino-2-(hydroxyimino)-1,1-dimethylethylcarbamate (2.0 g, 8.0 mmol) was dissolved in 30 mL MeOH, dimethyl acetylenedicarboxylate (DMAD, 1.1 mL, 9.0 mmol) was added slowly. The mixture was stirred for 2 h at room temperature, and then concentrated under reduced pressure to give a white oil. The mixture of the oil and 80 mL xylene was stirred at 90 °C for 2 h and 120 °C for 2 h, then refluxed for 12 h under nitrogen, concentrated to yield the crude product. The crude product was recrystallized with 2 mL MeOH and 10 mL tert-butyl methyl ether to afford 5 as a yellow solid (1.7 g, 58 percent): 1H-NMR (DMSO-d6) δ: 7.35 (m, 5H), 5.00 (s, 2H), 3.83 (s, 3H), 1.48 (s, 6H); ESI-MS m/z 360 (M), 384 (M+Na) +.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7114 - 7118
  • 35
  • [ 455-14-1 ]
  • [ 762-42-5 ]
  • [ 123158-31-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 6, p. 1323 - 1331
[2] Organic Letters, 2018, vol. 20, # 7, p. 1893 - 1897
[3] Patent: US5270309, 1993, A,
  • 36
  • [ 762-42-5 ]
  • [ 1222174-92-6 ]
Reference: [1] Patent: WO2012/122340, 2012, A1,
  • 37
  • [ 762-42-5 ]
  • [ 1239726-11-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7636 - 7649
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