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[ CAS No. 53055-05-3 ]

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Chemical Structure| 53055-05-3
Chemical Structure| 53055-05-3
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CAS No. :53055-05-3 MDL No. :MFCD00007135
Formula : C8H7NO4 Boiling Point : 344.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :181.15 g/mol Pubchem ID :98867
Synonyms :

Safety of [ 53055-05-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53055-05-3 ]

  • Upstream synthesis route of [ 53055-05-3 ]
  • Downstream synthetic route of [ 53055-05-3 ]

[ 53055-05-3 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 53055-05-3 ]
  • [ 84575-27-9 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 523
[2] Patent: DE215785, , ,
  • 2
  • [ 53055-05-3 ]
  • [ 708-15-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3515 - 3527
  • 3
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 134
[2] Journal of the Chemical Society, 1927, p. 2381
[3] Journal of the Chemical Society, 1926, p. 154[4] Journal of the Chemical Society, 1927, p. 2380
[5] Journal of the Chemical Society, 1932, p. 1112,1115
[6] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
  • 4
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 5
  • [ 591-31-1 ]
  • [ 53055-05-3 ]
Reference: [1] Chemische Berichte, 1895, vol. 28, p. 1385
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1889, vol. 22, p. 2354
[4] Journal of the Chemical Society, 1926, p. 154[5] Journal of the Chemical Society, 1927, p. 2380
[6] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
[7] Journal of the Chemical Society, 1932, p. 1112,1115
[8] Journal of the Chemical Society, 1937, p. 937,939
[9] Israel Journal of Chemistry, 1967, vol. 5, p. 129 - 136
[10] Organic Letters, 2006, vol. 8, # 14, p. 3117 - 3120
[11] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2664 - 2671
  • 6
  • [ 100-83-4 ]
  • [ 53055-05-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
  • 7
  • [ 100-83-4 ]
  • [ 77-78-1 ]
  • [ 53055-05-3 ]
Reference: [1] Monatshefte fuer Chemie, 1960, vol. 91, p. 1152 - 1161
  • 8
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 134
[2] Journal of the Chemical Society, 1927, p. 2381
[3] Journal of the Chemical Society, 1926, p. 154[4] Journal of the Chemical Society, 1927, p. 2380
[5] Journal of the Chemical Society, 1932, p. 1112,1115
[6] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
  • 9
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 10
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 53055-05-3 ]
Reference: [1] Journal of the Chemical Society, 1932, p. 1112,1115
  • 11
  • [ 53055-05-3 ]
  • [ 33852-43-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653
  • 12
  • [ 53055-05-3 ]
  • [ 4920-80-3 ]
  • [ 129841-09-4 ]
Reference: [1] Journal of Fluorine Chemistry, 2007, vol. 128, # 12, p. 1461 - 1468
  • 13
  • [ 53055-05-3 ]
  • [ 4920-80-3 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 2354
[2] Chemische Berichte, 1889, vol. 22, p. 2354
  • 14
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 15
  • [ 53055-05-3 ]
  • [ 70127-96-7 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogenchloride; iron; acetic acid In ethanol at 0℃; for 0.333333 h; Heating / reflux Example 2 Step 1. Preparation of 2-chloro-8-methoxyquinazolineStep 1. Preparation of 2-amino-3-methoxybenzaldehydeIron powder (40 g) was slowly added to a stirred solution of 3-methoxy-2-nitrobenzaldehyde (1) (70 g, 386 mmole) in AcOH gal. (100 mL) and EtOH abs. (400 mL). The reaction was cooled using an ice bath followed by addition of con. HCL (1 mL). The reaction became exothermic. After stabilization of the reaction temperature, the reaction was heated to reflux. The reaction reached completion after ca. 20 minutes according to LCMS. The reaction mixture was cooled to RT and filtered. The filtrate was evaporated to a thick brown syrup. The dark residue was dissolved in EtOAc (500 mL) and water (200 mL). The mixture was basified with NaOH 6M to ca. pH 10. The mixture was filtered over celite and the layers separated. The organic layer was washed with NaHCO3 (2 x 100 mL), water (2 x 100 mL), brine (100 mL), dried (Na2SO4), filtered and evaporated to a dark amber oil. The oil was dried in vacuo to give 95percent pure product 2-amino-3-methoxybenzaldehyde in 64percent yield (37.2 g, 246 mmole).
24% With ammonium chloride; zinc In ethanol at 70℃; for 3 h; To a solution of 3-methoxy-2-nitrobenzaldehyde (15.0 g, 83 mmol) in ethanol (450 mL) was added ammonium chloride (31.0 g, 580 mmol) and zinc powder (43.3 g, 662 mmol). The reaction mixture was heated at 70 °C for 3 h. The reaction mixture was cooled to room temperature and was filtered through a pad of Celite. The filtratewas concentrated and the residue was purified by column chromatography on silica gel (20percent —* 30percent ethyl acetate in hexanes) to afford 2-amino-3- methoxybenzaldehyde (2.94 g, 24percent yield) as a yellow oil: ‘H NMR (400 MHz, CDC13) ö 9.91 (s, 1H), 7.15 (dd, J 8.0, 1.2 Hz, 1H), 6.90 (dd, J 7.7, 0.9 Hz, 1H), 6.71 (t, J 7.9 Hz, 2H), 6.42 (br s, 2H), 3.91 (s, 3H); MS (ESI) m/e 152.1 [(M+H),calcd for C8H10NO2 152.1].
Reference: [1] Inorganic Chemistry, 2011, vol. 50, # 21, p. 10966 - 10973
[2] Patent: WO2007/117607, 2007, A2, . Location in patent: Page/Page column 306
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3515 - 3527
[4] Patent: WO2016/53794, 2016, A1, . Location in patent: Page/Page column 63; 64
[5] Journal of the Chemical Society, 1925, vol. 127, p. 876,877[6] Journal of the Chemical Society, 1926, p. 150
[7] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 211
[8] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2> 114, p. 231,235
[9] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 856 - 865
[10] Patent: US2003/97000, 2003, A1,
[11] Patent: US6617336, 2003, B1,
[12] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2664 - 2671
  • 16
  • [ 53055-05-3 ]
  • [ 70127-96-7 ]
  • [ 122528-40-9 ]
YieldReaction ConditionsOperation in experiment
53% With vasicine In ethylene glycol at 80℃; for 48 h; General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2137 - 2140
[2] Tetrahedron Letters, 2016, vol. 57, # 45, p. 5003 - 5008
[3] Tetrahedron Letters, 2006, vol. 47, # 41, p. 7295 - 7299
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