52407-43-9|1-Benzofuran-3-ylacetonitrile| Ambeed

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 1~51

1
[ 7169-34-8 ]
[ 2537-48-6 ]
[ 52407-43-9 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.
[2]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.
[3]Patent: US4835276,1989,A .
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 1176 - 1183.
[5]Journal of Organic Chemistry,2004,vol. 69,p. 5302 - 5306.
[6]Patent: US4916223,1990,A .
[7]Patent: US4673680,1987,A .
[8]Patent: US4710504,1987,A .
[9]Patent: US4831035,1989,A .
[10]Patent: US4690928,1987,A .

2
[ 52407-43-9 ]
[ 27404-31-5 ]

Yield	Reaction Conditions	Operation 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+).

References: [1]Patent: US4835276,1989,A .
[2]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.
[3]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.
[4]Patent: US4916223,1990,A .
[5]Patent: US4686226,1987,A .
[6]Patent: US4710504,1987,A .
[7]Patent: US4831035,1989,A .
[8]Patent: US4690928,1987,A .
[9]Patent: US2005/54634,2005,A1 .

3
[ 52407-43-9 ]
[ 64175-51-5 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

4
[ 52407-43-9 ]
[ 139313-76-1 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1176 - 1183.

5
[ 40052-96-8 ]
[ 372-09-8 ]
[ 52407-43-9 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

Yield	Reaction Conditions	Operation 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 ]

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.

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 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 5302 - 5306.
[2]Journal of Organic Chemistry,2004,vol. 69,p. 5302 - 5306.

10
[ 52407-43-9 ]
(2-fluoro-2-hydrobenzofuran-3-ylidene)acetonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 5302 - 5306.

11
[ 52407-43-9 ]
<i>N</i>-(2-benzofuran-3-yl-ethyl)-acrylamide [ No CAS ]

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.

12
[ 52407-43-9 ]
N-[2-(benzo[b]furan-3-yl)ethyl]vinylacetamide [ No CAS ]

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.

13
[ 52407-43-9 ]
N-[2-(benzo[b]furan-3-yl)ethyl]phenylacetamide [ No CAS ]

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.

14
[ 52407-43-9 ]
<i>N</i>-(2-benzofuran-3-yl-ethyl)-2-(3,4-dichloro-phenyl)-acetamide [ No CAS ]

References: [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181.

15
[ 52407-43-9 ]
[ 97456-65-0 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

16
[ 52407-43-9 ]
[ 98678-87-6 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

17
[ 52407-43-9 ]
[ 100480-86-2 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

18
[ 52407-43-9 ]
[ 100480-87-3 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

19
[ 52407-43-9 ]
[ 98678-88-7 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

20
[ 52407-43-9 ]
[ 98678-89-8 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759.

21
[ 52407-43-9 ]
[ 128104-98-3 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1176 - 1183.

22
[ 7169-34-8 ]
[ 52407-43-9 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

23
[ 52407-43-9 ]
[ 63703-24-2 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

24
[ 52407-43-9 ]
[ 82156-58-9 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

25
[ 52407-43-9 ]
[ 75611-06-2 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

26
[ 52407-43-9 ]
[ 136229-40-8 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

27
[ 52407-43-9 ]
[ 136229-46-4 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.
[2]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

28
[ 52407-43-9 ]
[ 136229-44-2 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

29
[ 52407-43-9 ]
[ 136229-43-1 ]

References: [1]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.
[2]Australian Journal of Chemistry,1991,vol. 44,p. 907 - 917.

30
[ 52407-43-9 ]
[ 4435-14-7 ]
[ 128104-98-3 ]

Yield	Reaction Conditions	Operation 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).

References: [1]Patent: US4895860,1990,A .

31
[ 2537-48-6 ]
[ 52407-43-9 ]

Yield	Reaction Conditions	Operation 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).

References: [1]Patent: US4895860,1990,A .

32
[ 52407-43-9 ]
[ 187804-19-9 ]

Yield	Reaction Conditions	Operation 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+)

References: [1]Patent: EP1224932,2002,A1 .

33
[ 500-22-1 ]
[ 52407-43-9 ]
(Z)-2-(benzo[b]furan-3-yl)-3-(pyridin-4-yl)acrylonitrile [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8228 - 8231.

34
[ 52407-43-9 ]
[ 1449744-25-5 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 12576 - 12579.

35
[ 52407-43-9 ]
[ 1449744-09-5 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 12576 - 12579.

36
[ 52407-43-9 ]
n-propyl halide [ No CAS ]
C₁₆H₁₉NO [ No CAS ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 12576 - 12579.

37
[ 52407-43-9 ]
[ 106-89-8 ]
C₁₃H₁₁NO₂ [ No CAS ]
C₁₃H₁₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A cooled (3 C.) stirred suspension of sodium amide (1.37 g, 35 mmol) in anhydrous THF (45 mL) under nitrogen was treated with a solution of <strong>[52407-43-9]benzofuran-3-acetonitrile</strong> (2.36 g, 15 mmol) in anhydrous THF (15 mL), stirred 1 h at room temperature, and recooled (3 C.). Epichlorohydrin (1.53 mL, 19.5 mmol) was added, and the mixture stirred at room temperature for 1 h, then cooled on an ice bath and quenched with saturated aqueous ammonium chloride (15 mL). After stirring for 15 min, the mixture was taken up in ethyl acetate (150 mL) and the organic layer separated. The aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined organic solution was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in methylene chloride and loaded onto a silica gel column (150 cc) and eluted with 5% ethyl acetate/methylene chloride, then 10% ethyl acetate/methylene chloride to afford the intermediate cyanocyclopropanemethanol (1.83 g, 57%) as a pale amber oil, a 2:1 E/Z mixture of isomers (by NMR).

References: [1]Patent: US2014/303207,2014,A1 .Location in patent: Paragraph 0187.

38
[ 52407-43-9 ]
[ 154357-93-4 ]
2-(2-(bromodifluoromethyl)benzofuran-3-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With tert.-butylhydroperoxide; In decane; dichloromethane; acetonitrile; at 20℃; for 16h;	General procedure: To a solution of substrate 1 (1.0 mmol, 1 equiv), NaSO2CF2Br (23.4 mg, 2.0 mmol, 2.0 equiv) in CH2Cl2 (7.0 mL) and CH3CN (3.5 mL) at room temperature was slowly added TBHP (5.0-6.0 M in decane, 1.4 mL, 7 equiv). The reaction was then stirred for 16 h. After the reaction was complete, the reaction mixture was concentrated under vacuum and the crude product was purified by column chromatography on silica gel to give the product.

References: [1]Tetrahedron Letters,2016,vol. 57,p. 2462 - 2464.

39
[ 52407-43-9 ]
[ 401-55-8 ]
ethyl 2-(3-(cyanomethyl)benzofuran-2-yl)-2-fluoroacetate [ No CAS ]

References: [1]New Journal of Chemistry,2016,vol. 40,p. 6564 - 6567.

40
[ 52407-43-9 ]
[ 119-53-9 ]
2-(benzofuran-3-ylmethyl)-4,5-diphenyloxazole [ No CAS ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 11926 - 11935.

41
[ 52407-43-9 ]
[ 7473-98-5 ]
C₂₀H₁₆O₃ [ No CAS ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 11926 - 11935.

42
[ 52407-43-9 ]
[ 2058-74-4 ]
2-(benzofuran-3-yl)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)-acetonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 4000 - 4008.

43
[ 52407-43-9 ]
[ 124-38-9 ]
2-(benzofuran-3-yl)propanenitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 9744 - 9749.

44
potassium cyanide [ No CAS ]
[ 67713-99-9 ]
[ 52407-43-9 ]

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

45
[ 271-89-6 ]
[ 52407-43-9 ]

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

46
[ 52407-43-9 ]
[ 5381-78-2 ]
3-methyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.3-Methyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile (3a). Yield (79%), shinyyellow needles, mp 322-324C (from EtOH). IR spectrum:ν 2225 cm-1 (C≡N). 1H NMR spectrum (CDCl3),δ, ppm: 4.29 s (3H, NCH3), 7.47 t.d (1H, Harom, J = 7.8,0.7 Hz), 7.52 d (1H, Harom, J = 8.2 Hz), 7.78 t.d (1H,Harom, J = 7.8, 1.4 Hz), 8.02 d (1H, Harom, J = 9.0 Hz),8.06 d (1H, Harom, J = 9.0 Hz), 8.27 s (1H, Harom),9.02 d (1H, Harom). 13C NMR spectrum (CDCl3), δC,ppm: 31.3, 103.7, 107.6, 113.3, 114.7, 118.1, 118.8,119.2, 121.4, 122.7, 123.8, 128.3, 129.2, 135.2, 140.6,143.1, 144.0, 148.9. Mass spectrum: m/z 298 [M]+.Found, %: C 72.61; H 3.41; N 18.50. C18H10N4O.Calculated, %: C 72.48; H 3.38; N 18.78. M 298.3.

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

47
[ 52407-43-9 ]
[ 90349-15-8 ]
3-ethyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

48
[ 52407-43-9 ]
[ 90840-34-9 ]
3-propyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

49
[ 52407-43-9 ]
[ 69015-43-6 ]
3-butyl-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]-quinoline-12-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

50
[ 52407-43-9 ]
C₁₁H₁₃N₃O₂ [ No CAS ]
3-(2-methylpropyl)-3H-[1]benzofuro[2,3-b]imidazo[4,5-f]quinoline-12-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: 1-Alkyl-5-nitro-1H-benzimidazole1a-1e (5 mmol) and <strong>[52407-43-9]2-(1-benzofuran-3-yl)acetonitrile</strong>(2, 0.942 g, 6 mmol) were added with stirring to a solutionof potassium hydroxide (10 g, 178 mmol) inmetha nol (30 mL). The mixture was stirred at roomtemperature for 24 h and concentrated under reducedpressure, and the precipitate was collected by filtration,washed in succession with water, cold ethanol, andacetone, and air-dried. The product was purified byrecrystallization from ethanol.

References: [1]Russian Journal of Organic Chemistry,2021,vol. 57,p. 440 - 447.
Zh. Org. Khim.,.

51
[ 52407-43-9 ]
[ 56669-96-6 ]
3-benzofuran-3-yl-N₇,N₇-dimethylquinoline-2,7-diamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 12152 - 12162.

Historical Records

Technical Information

• Blaise Reaction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Hydride Reductions • Preparation of Aldehydes and Ketones • Preparation of Amines • Ritter Reaction • Thorpe-Ziegler Reaction

Related Functional Groups of
[ 52407-43-9 ]

Nitriles

A210611 [37813-04-0]

2-(Benzofuran-5-yl)acetonitrile

Similarity: 0.86

A469328 [3782-07-8]

2-(2,3-Dimethylbenzofuran-5-yl)acetonitrile

Similarity: 0.80

Related Parent Nucleus of
[ 52407-43-9 ]

Benzofurans

A826908 [36724-24-0]

3-Ethylbenzofuran

Similarity: 0.88

A213272 [25252-19-1]

3-(tert-Butyl)benzofuran

Similarity: 0.86

A701141 [71507-43-2]

6-Ethyl-3-methylbenzofuran

Similarity: 0.86

A210611 [37813-04-0]

2-(Benzofuran-5-yl)acetonitrile

Similarity: 0.86

A826330 [105540-41-8]

3-Isopropyl-5-methylbenzofuran

Similarity: 0.84

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CAS No.: 52407-43-9

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