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[ CAS No. 17403-47-3 ]

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2D
Chemical Structure| 17403-47-3
Chemical Structure| 17403-47-3
Structure of 17403-47-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 17403-47-3 ]

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Product Details of [ 17403-47-3 ]

CAS No. :17403-47-3MDL No. :MFCD22376562
Formula : C8H7NO3 Boiling Point : 292.3±29.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :TYPKKUFDAHEIOP-UHFFFAOYSA-N
M.W :165.15Pubchem ID :21816585
Synonyms :

Computed Properties of [ 17403-47-3 ]

TPSA : 55 H-Bond Acceptor Count : 3
XLogP3 : 1.8 H-Bond Donor Count : 0
SP3 : 0.25 Rotatable Bond Count : 0

Safety of [ 17403-47-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17403-47-3 ]

  • Upstream synthesis route of [ 17403-47-3 ]
  • Downstream synthetic route of [ 17403-47-3 ]

[ 17403-47-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 496-16-2 ]
  • [ 17403-47-3 ]
YieldReaction ConditionsOperation in experiment
54% With silver nitrate; acetyl chloride In water; acetonitrile at 0 - 20℃; for 5.00 h; Silver nitrate (1.41 g, 8.32 mmol) and coumaran 3 (0.59 mL, 8.32 mmol) were dissolved in acetonitrile (10 mL) and placed in a 100 mL three-necked flask equipped with a dropping funnel, condenser and drying tube, and thermometer. 0.59 mL (8.32 mmol) of acetyl chloride was added to the reaction mixture at 0°C. As the quantity of silver chloride increased, further dilution with acetonitrile and more vigorous stirring were used to help maintain reactant contact for 1 h at 0–5°C and for 4 h at room temperature. 20 mL of water was added to the reaction flask at 0°C and then an additional 10 mL of water was added when the mixture was at room temperature. Exhaustive treatments of solid and liquid materials with ethyl acetate were used to extract the products. The organic layer was concentrated, dried over MgSO4, and then purified by column chromatography(EA/n-hexane) to give 740 mg of 5 (54percent) as a yellow solid.
44.4% at 65 - 75℃; for 0.50 h; Example 14: Preparation of (R)-2-[[[4-(3-methoxylpropoxy)-3-methyl-2-pyridyl]methyl]-sulfinyl]-6,7-dihydro-3H-benzofuro[5,6-d]imidazole sodium (sodium salt of Compound 30) Step 1: Preparation of 5-nitro-2,3-dihydrobenzofuran [Show Image] 2,3-Dihydrobenzofuran (36 g, 0.3 mol) was added to glacial acetic acid (100 mL), heated to 65°C, then concentrated nitric acid (25 mL, 0.36 mol) was added dropwise into the reaction solution, the temperature of the reaction solution was controlled at 65-75°C. After the end of dropwise addition, the agitation was kept for 0.5 h. It was then cooled to room temperature, filtered, washed with water, and dried to obtain a product (22 g, 44.4percent).
29% With nitric acid; acetic acid In water at 70℃; for 0.50 h; To a solution of 25.5 g (0.212 mol) of 2, 3-dihydrobenzofuran in 175 mL of acetic acid was added about one quarter of 4.5 mL (0.227 mol) of 70percent aqueous nitric acid dropwise. The reaction was monitored by TLC (EtOAc-hexanes (15: 85) ). The mixture was warmed to 70°C where the reaction began. The remainder of the nitric acid was then added while maintaining the reaction at 70°C. After 30 minutes, the reaction was cooled and poured into 1.5 L of ice water. The black solid was collected by filtration washing with water. The solid was partitioned between 500 mL of saturated aqueous sodium bicarbonate and 150 mL of EtOAc. The aqueous layer was separated and extracted with three 150 mL portions of EtOAc. The combined organic layers were washed with three 100 mL portions of saturated aqueous sodium bicarbonate, 100 mL of saturated aqueous ammonium chloride, 100 mL of brine, dried over magnesium sulfate, filtered, and concentrated to afford a red oil/solid. The mixture was dissolved in dichloromethane and passed through a pad of silica gel eluting with dichloromethane and concentrated. The resulting red mixture was triturated with ether-hexanes (1: 1) and filtered to afford 10.5 g (29percent) of 5-nitro-2, 3-dihydrobenzofuran as a tan solid.
17% at 0 - 20℃; for 2.00 h; To a solution of 20 (27.1 g, 226 mmol) in acetic acid (100 mL) was slowly added nitric acid (11.2 mL, 249 mmol) at 0 °C. After stirring at room temperature for 2 h, the reaction mixture was poured into a mixture of ice and 12 N NaOH (100 mL). The mixture was extracted with EtOAc. The extract was washed with aqueous NH4Cl and brine, dried and concentrated. The residue was purified by flash chromatography on SiO2 with an eluent of 20percent EtOAc/hexane to provide 21 (6.4 g, 17percent) as a pale brown powder; 1H NMR (CDCl3) δ: 3.30 (2H, t, J = 8.7 Hz), 4.74 (2H, t, J = 8.7 Hz), 6.81 (1H, d, J = 9.6 Hz), 8.07-8.12 (2H, m); Anal. Calcd for C8H7NO: C, 58.18; H, 4.27; N, 8.48. Found: C, 57.93; H, 4.19; N, 8.27.

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[3] Patent: EP2532665, 2012, A1. Location in patent: Page/Page column 41
[4] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 138-139
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6681 - 6698
[6] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
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  • [ 7169-34-8 ]
  • [ 17403-47-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
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