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Chemical Structure| 52407-43-9 Chemical Structure| 52407-43-9

Structure of 52407-43-9

Chemical Structure| 52407-43-9

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Product Details of [ 52407-43-9 ]

CAS No. :52407-43-9
Formula : C10H7NO
M.W : 157.17
SMILES Code : N#CCC1=COC2=C1C=CC=C2
MDL No. :MFCD02183555
InChI Key :BJAJKVZABJZXDC-UHFFFAOYSA-N
Pubchem ID :2769401

Safety of [ 52407-43-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 52407-43-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 52407-43-9 ]

[ 52407-43-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 7169-34-8 ]
  • [ 2537-48-6 ]
  • [ 52407-43-9 ]
YieldReaction ConditionsOperation in experiment
66% With hydrogenchloride; In tetrahydrofuran; Step A: Preparation of 3-Cyanomethylbenzo[b]furan STR8 To a suspension of 27 gms (1.12 mole) of oil free sodium hydride in 400 ml of tetrahydrofuran (THF) was added dropwise a solution of 199.2 gms (1.12 mole) of diethylcyanomethylphosphonate in 400 mL of THF. After the H2 evolution had ceased, a solution of 150.1 g (1.12 mole) of 3-(2H)-benzo[b]-furanone in 1 L of THF was added. The solution was heated at 70 C. for 1.5 hours, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 110-120 C./0.7 Torr Hg to give 116 g (66% yield) of a yellow oil which crystallized upon standing.
With hydrogenchloride; In tetrahydrofuran; Step A: Preparation of 3-Cyanomethylbenzo[b]furan To a suspension of 2.64 grams (0.11 mole) of oil free sodium hydride in 200 milliliters of tetrahydrofuran (THF) was added dropwise a solution of 19.47 grams (0.11 mole) of diethyl cyanomethylphosphonate in 75 milliliters of THF. After the H2 evolution had ceased, a solution of 13.4 grams (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 milliliters of THF was added. The solution was heated at 70 C. for 1.5 hours, cooled, and poured into 500 milliliters of 5% HCl, and worked up using conventional procedures and finally distilled at 96-100 C./0.075 mm Hg to obtain a yellow oil product which crystallized upon standing.
With hydrogenchloride; In tetrahydrofuran; Step A: Preparation of 3-Cyanomethylbenzo[b]furan To a suspension of 2.64 gms (0.11 mole) of oil free sodium hydride in 200 ml of tetrahydrofuran (THF) was added dropwise a solution of 19.47 gms (0.11 mole) of diethylcyanomethylphosphonate in 75 mL of THF. After the H2 evolution had ceased, a solution of 13.4 g (0.1 mole) of 3-(2H)-benzo[b]-furanone in 100 mL of THF was added. The solution was heated at 70 C. for 1.5 hrs, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 96-100 C./0.075 mm Hg to give 10.85 g of a yellow oil which crystallized upon standing.
With hydrogenchloride; In tetrahydrofuran; Step A: Preparation of 3-Cyanomethylbenzo[b]furan To a suspension of 2.64 gms (0.11 mole) of oil free sodium hydride in 200 ml of tetrahydrofuran (THF) was added dropwise a solution of 19.47 gms (0.11 mole) of diethylcyanomethylphosphonate in 75 mL of THF. After the H2 evolution had ceased, a solution of 13.4 g (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 mL of THF was added. The solution was heated at 70 C. for 1.5 hours, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 96-100 C./0.075 mm Hg to give 10.85 g of a yellow oil which crystallized upon standing.
With hydrogenchloride; In tetrahydrofuran; Step A Preparation of 3-Cyanomethylbenzo[b]furan To a suspension of 2.64 grams (0.11 mole) of oil free sodium hydride in 200 milliliters of tetrahydrofuran (THF) was added dropwise a solution of 19.47 grams (0.11 mole) of diethyl cyanomethylphosphonate in 75 milliliters of THF. After the H2 evolution had ceased, a solution of 13.4 grams (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 milliliters of THF was added. The solution was heated at 70 C. for 1.5 hours, cooled, and poured into 500 milliliters of 5% HCl, and worked up using conventional procedures and finally distilled at 96-100 C./0.075 mm Hg to obtain a yellow oil productwhich crystallized upon standing.
With hydrogenchloride; In tetrahydrofuran; Step A Preparation of 3-Cyanomethylbenzo[b]furan To a suspension of 2.64 gms (0.11 mole) of oil free sodium hydride in 200 ml of tetrahydrofuran (THF) was added dropwise a solution of 19.47 gms (0.11 mole) of diethylcyanomethylphosphonate in 75 mL of THF. After the H2 evolution had ceased, a solution of 13.4 g (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 mL of THF was added. The solution was heated at 70 C. for 1.5 hours, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 96-100 C./0.075 mm Hg to give 10.85 g of a yellow oil which crystallized upon standing.

  • 2
  • [ 52407-43-9 ]
  • [ 27404-31-5 ]
YieldReaction ConditionsOperation in experiment
71% aluminum nickel; In methanol; Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine STR9 To a solution of 3.1 g of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 40 mL of methanol was added 2.4 g of Raney nickel. The reaction was agitated at 25 C. in a Parr apparatus under 40 psi hydrogen for 21/2 hours. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 2.2 g (71% yield) of oily product.
In diethyl ether; water; Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 grams (0.025 mole) of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 200 milliliters of diethyl ether was slowly added to a refluxing suspension of 3.84 grams (0.1 mole) of lithium aluminum hydride in 400 milliliters of ether and the mixture was heated 3 hours, then cooled and water was slowly added. The suspension was filtered and the filtrate was evaporated to obtain an oily product, the hydrochloride salt of which has m.p. 183-185 C.
In diethyl ether; water; Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hrs., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.
In diethyl ether; water; Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hours., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.
In diethyl ether; water; Step B Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 grams (0.025 mole) of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 200 milliliters of diethyl ether was slowly added to a refluxing suspension of 3.84 grams (0.1 mole) of lithium aluminum hydride in 400 milliliters of ether and the mixture was heated 3 hours, then cooled and water was slowly added. The suspension was filtered and the filtrate was evaporated to obtain an oily product, the hydrochloride salt of which has m.p. 183-185 C.
In diethyl ether; water; Step B Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of <strong>[52407-43-9]3-cyanomethylbenzo[b]furan</strong> in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hours., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.
A. In a manner similar to that described in Step D of Example 32, but replacing 2-(1-tert-butoxycarbonyl indol-3-yl) propionitrile with 3-benzofuranylacetonitrile, the intermediate 3(2-aminoethyl) benzofuran was prepared; MS (ES): 162 (MH+).

  • 3
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  • [ 64175-51-5 ]
  • 4
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  • [ 139313-76-1 ]
  • 5
  • [ 40052-96-8 ]
  • [ 372-09-8 ]
  • [ 52407-43-9 ]
YieldReaction ConditionsOperation in experiment
91% Preparation 129 1-Benzofuran-3-ylacetonitrile Sodium hydride (268 mg, 6.7 mmol) was slurried in dry THF (10 ml) at 0 C. under nitrogen and diethyl cyanomethyl phosphonate (1.1 ml, 6.7 mmol) added dropwise and the whole stirred for 45 min. 3-Coumaranone (Lancaster) (900 mg, 6.7 mmol) was then added dropwise and the whole stirred at room temperature for 45 min. The reaction was diluted with EtOAc (15 ml) and water (15 ml), and the organic layer was then separated, dried (MgSO4) and evaporated and the residue flash chromatographed using 0-5% EtOAc in pentane to give the title product (940 mg, 91%); 1H-NMR (400 MHz, CDCl3) δ: 3.77 (s, 2H), 7.25-7.40 (m, 2H), 7.52 (dd, 1H), 7.58 (dd, 1H), 7.67 (s, 1H); LRMS: M+NH4+, 175. (TS+).
Preparation 130 2-(1-Benzofuran-3-yl)-ethylamine The product from Preparation 129 (400 mg, 2.55 mmol) was combined with ammonium hydroxide solution (10 ml), ethanol (20 ml) and 30wt % Ra-Ni (120 mg, cat.) and hydrogenated at 30p.s.i. hydrogen pressure at room temperature for 16 h.
116 g (66%) Step A: Preparation of 3-Cyanomethylbenzo[b]furan STR8 NaH (54 g of a 50% oil suspension; 1.12 mol) was placed in a 3 L 3-neck RB flask equipped with a mechanical stirrer and washed twice with hexane. Dry THF (400 ml) was added followed by the dropwise addition of a solution of diethylcyanomethyl phosphonate (199.2 g; 1.12 mol) in 400 ml of THF. After the addition was complete, the reaction was stirred an additional 30 minutes until gas evolution ceased. A solution of 1 (150.1 g; 1.12 mol) in 1 L of THF was added dropwise at room temperature. The reaction was refluxed for 1.5 hours. After cooling, the solvent was removed in vacuo. The residue was dissolved in ether and acidified with concentrated HCl. The ether layer was washed with 6N HCl (3*300 ml), H2 O, brine, dried (Na2 SO4), filtered, and concentrated. The crude product was distilled to afford 116 g (66%) of 2 b.p. (0.7 Torr) 110-120 C.
  • 8
  • [ 52407-43-9 ]
  • N-2-(benzo[b]furan-3-yl)ethylamine hydrochloride [ No CAS ]
  • 9
  • [ 52407-43-9 ]
  • (2-fluoro-2-hydrobenzofuran-3-ylidene)acetonitrile [ No CAS ]
  • trans-(2,3-difluoro-2,3-dihydro-3-benzofuranyl)acetonitrile [ No CAS ]
  • cis-(2,3-difluoro-2,3-dihydro-3-benzofuranyl)acetonitrile [ No CAS ]
  • 10
  • [ 52407-43-9 ]
  • (2-fluoro-2-hydrobenzofuran-3-ylidene)acetonitrile [ No CAS ]
  • 11
  • [ 52407-43-9 ]
  • <i>N</i>-(2-benzofuran-3-yl-ethyl)-acrylamide [ No CAS ]
  • 12
  • [ 52407-43-9 ]
  • N-[2-(benzo[b]furan-3-yl)ethyl]vinylacetamide [ No CAS ]
  • 13
  • [ 52407-43-9 ]
  • N-[2-(benzo[b]furan-3-yl)ethyl]phenylacetamide [ No CAS ]
  • 14
  • [ 52407-43-9 ]
  • <i>N</i>-(2-benzofuran-3-yl-ethyl)-2-(3,4-dichloro-phenyl)-acetamide [ No CAS ]
  • 15
  • [ 52407-43-9 ]
  • [ 97456-65-0 ]
  • 16
  • [ 52407-43-9 ]
  • [ 98678-87-6 ]
  • 17
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  • [ 100480-86-2 ]
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  • [ 100480-87-3 ]
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  • [ 98678-88-7 ]
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  • [ 98678-89-8 ]
  • 21
  • [ 52407-43-9 ]
  • [ 128104-98-3 ]
  • 22
  • [ 7169-34-8 ]
  • [ 52407-43-9 ]
  • 23
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  • [ 63703-24-2 ]
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  • [ 82156-58-9 ]
  • 25
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  • [ 75611-06-2 ]
  • 26
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  • [ 136229-40-8 ]
  • 28
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  • [ 136229-44-2 ]
  • 30
  • [ 52407-43-9 ]
  • [ 4435-14-7 ]
  • [ 128104-98-3 ]
YieldReaction ConditionsOperation in experiment
Step (2) Preparation of 4-[(3-Benzofuranyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-Oxide According to Scheme I illustrated by Example 4, 3-benzofuranylacetonitrile was converted to the desired product as beige crystals, m.p. 138.5-140 C. temperature. Cyclohexylacetonitrile (14.7 g, 120 mmol) was added in one portion and the resulting mixture was heated to reflux for 12 hours. The mixture was cooled to room temperature and concentrated to give a yellow solid. The solid was collected by filtration, washed with water, EtOAc/hexane (2:8), and dried in vacuo to give 7.4 g (40%) of the product of sufficient purity for use in the next reaction. NMR (DMSO-d6, 200 MHz): delta 0.85 (m, 2H), 1.10 (m, 3H), 1.64 (m, 6H), 1.80 (d, J=7.0, 2H), 5.25 (br s, 2H), 8.30 (br s, 1H).
  • 31
  • [ 2537-48-6 ]
  • [ 52407-43-9 ]
YieldReaction ConditionsOperation in experiment
6.67 g (100%) In tetrahydrofuran; hexane; Step (1) Preparation of 3-Benzofuranylacetonitrile To a stirred mixture of hexane washed sodium hydride (2.21 g, 0.046 mol, 50%/mineral oil) in THF (125 mL), was added diethyl cyanomethylphosphonate (8.15 g, 0.046 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour, 3-coumaranone (sublimed) (5.6 g, 0.042 mol) in THF (100 mL) was added dropwise at 0 C., and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with water (300 mL), and extracted with ether (800 mL). The extracts were washed with brine (2*100 mL), dried (MgSO4), and concentrated to yield 6.67 g (100%) of the product as an off-white solid. NMR (CDCl3, 200 MHz): δ 3.77 (s, 2H), 7.2-7.9 (m, 5H).
  • 32
  • [ 52407-43-9 ]
  • [ 187804-19-9 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; In tert-butyl alcohol; Referential Example 16 To a solution of <strong>[52407-43-9]benzofuran-3-acetonitrile</strong> (120 mg, 0.76 mmol) synthesised according to a known method (J. Med. Chem.,Vol. 35, p. 1176, 1992) in tert-butyl alcohol (2 mL) was added potassium hydride (340 mg, 6.08 mmol), and the whole was refluxed for 1.5 hours. After cooling to room temperature and acidification with 1N hydrochloric acid, resulting solid was filtrated, washed with water and diethyl ether gave benzofuran-3-acetamide (100 mg, 75%) as brown solid. 1H NMR(DMSO-d6) δ 3. 48(s, 2H), 6. 98(brs, 1H), 7. 25(t, J=7. 4Hz, 1H), 7. 31(t, J= 7. 4Hz, 1H), 7. 53(brs, 1H), 7. 54 (d, J=7. 4Hz, 1H), 7.63(d, J=7. 4Hz, 1H), 7. 81(s, 1H). IR(KBr) 3355, 3200, 1665, 1640, 1460, 1420, 1410, 1100, 755cm-1. MS m/z 175(M+)
  • 33
  • [ 500-22-1 ]
  • [ 52407-43-9 ]
  • (Z)-2-(benzo[b]furan-3-yl)-3-(pyridin-4-yl)acrylonitrile [ No CAS ]
  • 34
  • [ 52407-43-9 ]
  • [ 1449744-25-5 ]
  • 35
  • [ 52407-43-9 ]
  • [ 1449744-09-5 ]
 

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