[ CAS No. 174775-48-5 ]

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2D
Chemical Structure| 174775-48-5
Chemical Structure| 174775-48-5
Structure of 174775-48-5

Quality Control of [ 174775-48-5 ]

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Related Doc. of [ 174775-48-5 ]

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Product Details of [ 174775-48-5 ]

CAS No. :174775-48-5MDL No. :MFCD08275091
Formula :C11H11NO3Boiling Point :348.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :205.21Pubchem ID :9837138
Synonyms :

Computed Properties of [ 174775-48-5 ]

TPSA : 65.5 H-Bond Acceptor Count : 4
XLogP3 : 2.2 H-Bond Donor Count : 1
SP3 : 0.18 Rotatable Bond Count : 3

Safety of [ 174775-48-5 ]

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

Application In Synthesis of [ 174775-48-5 ]

  • Upstream synthesis route of [ 174775-48-5 ]
  • Downstream synthetic route of [ 174775-48-5 ]

[ 174775-48-5 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 33 - 38℃; Example-2: preparation of ethyl-5-amino-l-benzofuran-2-carboxylate To a solution of ethyl-5-nitro- 1 -benzofuran-2-carboxylate (100g) in Ethyl acetate (800ml) was added 10percent palladium on carbon (4.0g). The reaction mixture was stirred under an atmosphere of hydrogen at 33-38°C with 4-5kg/cm2 hydrogen pressure for 4-6 hrs. After completion of the reaction, reaction mixture was filtered through hyflo, washed with ethyl acetate. The filtrate was concentrated in vacuo to give ethyl-5-amino-l-benzofuran-2- carboxylate yield: 100percent
100% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 33 - 38℃; To a solution of ethyl-5-nitro-1-benzofuran-2-carboxylate (100 g) in Ethyl acetate (800 ml) was added 10percent palladium on carbon (4.0 g).
The reaction mixture was stirred under an atmosphere of hydrogen at 33-38° C. with 4-5 kg/cm2 hydrogen pressure for 4-6 hrs.
After completion of the reaction, reaction mixture was filtered through hyflo, washed with ethyl acetate.
The filtrate was concentrated in vacuo to give ethyl-5-amino-1-benzofuran-2-carboxylate yield: 100percent
98% With 5%-palladium/activated carbon; hydrogen In ethanol at 10 - 30℃; for 3.00 h; 20.0g of ethyl 5-nitrobenzofuran-2-carboxylate prepared in Example 2 was added into a reaction flask, 300ml of ethanol was added, 2g of 5percent Pd on carbon was added, the mixture was replaced with hydrogen twice, and the hydrogen pressure was controlled to 0.3 -0.5MPa, 10-30 hydrogenation reaction for 3 hours, the reaction was completed, filtered and the filtrate was concentrated under reduced pressure to give dry 5-aminobenzofuran-2-carboxylic acid ethyl ester 17.1g, yield 98percent.
95.1% With 5%-palladium/activated carbon; hydrogen In ethanol at 30℃; for 3.00 h; Ethyl 2-nitrobenzofuran-2-carboxylate (23.5 g) prepared according to Example 4 was added to a reaction flask, 200 ml of ethanol was added, 3 g of 5percent palladium carbon was added, and the mixture was replaced with hydrogen 3 times.The hydrogen pressure was controlled to be 0.4-0.5 MPa, hydrogenation reaction was performed at 30° C. for 3 hours, the reaction was completed, and the reaction was filtered. The filtrate was concentrated under reduced pressure to dryness to obtain 19.5 g of 5-aminobenzofuran-2-carboxylic acid ethyl ester.Yield 95.1percent, purity 98.8percent.
82 g With 2.5% wt Pd/C; hydrogen In methanol at 25 - 50℃; Step A: Preparation of ethyl-5-amino-1-benzofuran-2-carboxylateEthyl-5-nitro-1-benzofuran-2-carboxylate (100 g) was added to methanol (500mL). 2.5percent (w/w) Palladiumlcarbon (10 g in 10 mL water) was added to the hydrogenator.The hydrogen gas was passed at a pressure of 1 to 4 kg/cm2 for 2 hours to 4 hours at 25°C to 50°C. The reaction mixture was filtered through a Celite® filter. The solvent was recovered under vacuum. A mixture of de-ionized water (500 mL) and dichloromethane (300 mL) was added to the reaction mixture and the layers obtained were separated. Theorganic layer was recovered under vacuum to obtain the title compound.Yield (Wet): 82 g

Reference: [1] Patent: WO2013/153492, 2013, A2. Location in patent: Page/Page column 23
[2] Patent: US2015/87835, 2015, A1. Location in patent: Paragraph 0125
[3] ChemCatChem, 2014, vol. 6, # 11, p. 3153 - 3159
[4] Patent: CN107674052, 2018, A. Location in patent: Paragraph 0035-0037
[5] Patent: CN107540646, 2018, A. Location in patent: Paragraph 0041; 0042; 0043
[6] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4684 - 4692
[7] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2675 - 2684
[8] Patent: WO2007/3961, 2007, A2. Location in patent: Page/Page column 25
[9] Patent: WO2005/32594, 2005, A2. Location in patent: Page/Page column 5; 29
[10] Journal of Medicinal Chemistry, 2008, vol. 51, # 11, p. 3133 - 3144
[11] Patent: WO2014/61000, 2014, A1. Location in patent: Page/Page column 14
[12] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6552 - 6563
[13] Patent: WO2005/32594, 2005, A2. Location in patent: Page/Page column 5; 29
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YieldReaction ConditionsOperation in experiment
91% With hydrogen In ethanol at 20℃; for 6.00 h; To the solution of ethyl 5-nitrobenzofuran-2-carboxylate (3) (1 mmol) in Ethanol solvent and degas with N2. Raney-Ni (3.0 mmol) was added to the reaction mass.
Then put H2 pressure.
The RM was stirred for 6hr at rt. RM was filter through the high-flow; the combined organic layer was evaporated to dryness.
Yellow solid, 91percent yield, mp 189.6-191.4 °C, 1H NMR (300 MHz, CDCl3): δ = 7.62 (s, 1H), 7.47 (d, J = 7.2 Hz, 1H), 6.74 (m, 2H), 4.35 (q, J = 7.5, 14.4 Hz, 2H), 1.33 (m, 3H) 6H); 13C NMR (75 MHz, DMSO+CDCl3): 157.3, 154.9, 142.5, 129.7, 120.8, 112.2, 110.4, 109.2, 107.2, 58.8, 13.2. MS calcd for C11H11NO3: 205.2. Found: 206.6, (M+). Anal. Calcd for C11H11NO3: C, 64.38; H, 5.40; N, 6.83. Found: C, 64.39; H, 5.42; N, 6.81.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4924 - 4934
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6552 - 6563
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Reference: [1] Patent: WO2013/153492, 2013, A2
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6552 - 6563
[3] Patent: US2015/87835, 2015, A1
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Reference: [1] Patent: CN107674052, 2018, A
[2] Patent: CN107674052, 2018, A
[3] Patent: CN107540646, 2018, A
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Reference: [1] Patent: CN107540646, 2018, A
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Reference: [1] Patent: CN107540646, 2018, A
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