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[ CAS No. 73368-41-9 ]

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Chemical Structure| 73368-41-9
Chemical Structure| 73368-41-9
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CAS No. :73368-41-9 MDL No. :MFCD14543019
Formula : C10H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :195.22 g/mol Pubchem ID :11788808
Synonyms :

Safety of [ 73368-41-9 ]

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

Application In Synthesis of [ 73368-41-9 ]

  • Upstream synthesis route of [ 73368-41-9 ]
  • Downstream synthetic route of [ 73368-41-9 ]

[ 73368-41-9 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
89.1% Reflux; Inert atmosphere; Cooling; Large scale A 22-L 3-necked RBF equipped with an electrical heating mantle, a thermocouple probe, overhead mechanical stirrer, water-cooled condenser, nitrogen bubbler and addition funnel was charged with 4-amino-3-methoxybenzoic acid (1.0 kg, 5.98 mol, 1.0 equiv.) and ethanol (200 proof) (10.0 L, 10 vol.) to produce a stirrable slurry. Without external cooling, sulfuric acid (1.17 kg, 0.64 L, 12.0 mol, 2.0 equiv.) was then added slowly over 1 h, the slurry initially goes thick, but breaks up and eventually all solids dissolve to form a dark solution. The exothermic addition increased the temperature to -45 °C; additional heating was then applied to bring the solution to reflux and was held at reflux overnight. An HPLC sample was taken and showed -5percent starting benzoic acid remaining. The reflux head was switched to full takeoff and 2.5 L was distilled off. The reaction was cooled to 6 °C in an ice bath and the pH slowly adjusted to 12 by the addition of a solution of sodium hydroxide (50 wt percent, 1.03 kg, 681 ml, 12.9 mol, 2.15 equiv.) in water (3.5 L) keeping the temperature below 20 °C. Following a 30 min. post-stir, an additional quantity of water (4.0 L) was added and stirred at ca. 10 °C for 30 min. The solid were filtered, washed thoroughly with water (4.0 L), and then vacuum dried at 65 °C overnight. The yield of ethyl 4- amino-3-methoxybenzoate was 1.04 kg (89.1percent) as a light brown solid. m.p.= 83-87 °C (DSC); 1H NMR (300 MHz, CDC13) δ 7.56 (1H, dd, J = 7.9, 1.5 Hz), 7.47 (1H, d J=1.5 Hz), 6.66 (1H, d, J= 7.9 Hz), 4.33 (2H, t, J= 7.2 Hz), 4.27 (1H, br s), 3.90 (3H), 1.37 (3H, t, J = 7.2 Hz).
Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 14, p. 3332 - 3339
[2] Patent: WO2014/128094, 2014, A1, . Location in patent: Page/Page column 22
[3] European Journal of Medicinal Chemistry, 2007, vol. 42, # 5, p. 567 - 579
[4] Patent: US2009/259049, 2009, A1, . Location in patent: Page/Page column 12
[5] Patent: US2011/86882, 2011, A1, . Location in patent: Page/Page column 27
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YieldReaction ConditionsOperation in experiment
7.5 g With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 12 h; [0553j To a solution of ethyl 3-methoxy-4-nitrobenzoate (5-B) (7.65 g, 34 mmol) in EtOH (20 mL) was added Pd/C (1.5 g), while stirring at rt under H2 for 12 h. The solid was removed by filtration and the mixture was extracted with EA. The solvent was removed to afford ethyl 4-amino-3-methoxybenzoate (5-C) (7.5 g).
Reference: [1] European Journal of Organic Chemistry, 2010, # 24, p. 4662 - 4670
[2] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2243 - 2246
[3] Patent: WO2014/31784, 2014, A1, . Location in patent: Paragraph 0553
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2243 - 2246
[2] Patent: WO2014/31784, 2014, A1,
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Reference: [1] Patent: US6024937, 2000, A,
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2243 - 2246
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2243 - 2246
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