Category: 77326-36-4

Reference of 77326-36-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium hydride 60% w/w in oil (87 mg, 2.28 mmol)was added portionwise to N-Boc-piperidine-2-methanol(0.49 g, 2.28 mmol) in THF (7.6 mL) at 0 oC over a period of 10 min.The resulting solution was stirred at 0 oC for 1 hr. Then 2-amino-6-fluorobenzonitrile(0.28 g, 2.05 mmol) was added in one-portion and the mixture heatedat 85 oC for 2 h. The reaction mixture was quenched with water (2mL) and then evaporated. The residue was diluted with ethyl acetate (30 mL) andwashed with a saturated aqueous solution of sodium bicarbonate (2 x 30 mL). Theorganic layer was dried over sodium sulphate, filtered and the solvent removed in vacuo. The residue was passed throughan SCX-2 ion exchange column (10 g) and the crude product eluted with 2Mammonia in methanol. Purification by flash column chromatography [SiO2,MeOH:DCM, 0-15%] afforded the corresponding product as a white powder (87 mg,0.38 mmol, 17%). Mp 102-103 oC; numax/cm-13311, 2925, 2211, 1577, 1476 and 1456; 1H NMR (500 MHz, CDCl3)delta = 7.18 (dd, J = 8.5 Hz, 1H), 6.30 (dd, J = 8.5, 1.0 Hz, 1H),6.20 (dd, J = 8.5, 1.0 Hz, 1H), 4.48 (s, 2H), 3.96 (dd, J = 9.0,3.7 Hz, 1H), 3.86 (dd, J = 9.0, 8.0 Hz, 1H), 3.14 (ddt, J = 11.5,4.0, 2.0 Hz, 1H), 3.10 – 2.97 (m, 1H), 2.78 (s, 1H), 2.71 (td, J = 11.9,2.7 Hz, 1H), 1.96 – 1.78 (m, 1H), 1.76 – 1.62 (m, 2H), 1.58 – 1.26 (m, 3H); 13CNMR (126 MHz, CDCl3) delta = 161.0, 151.1, 134.5, 115.4, 107.6, 100.4,86.7, 73.0, 55.4, 46.4, 28.3, 25.9, 24.1; LC-MS (TOF, 2.0 min) Rt= 0.59 min; m/z (ESI) 232 (M+H); Hi-Res LC-MS (ESI) m/z calcd for C13H18N3O (M+H) 232.1450, found 232.1452

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Amino-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hensbergen, Albertus Wijnand; Mills, Vanessa R.; Collins, Ian; Jones, Alan M.; Tetrahedron Letters; vol. 56; 46; (2015); p. 6478 – 6483;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 77326-36-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-amino-6-isobutoxybenzonitrile Sodium hydride (60% suspension in oil, 25.0 g, 0.625 mol) was suspended in anhydrous THF (1000 mL) under nitrogen and heated to an internal temperature of 40 C. to 45 C. 2-methylpropan-1-ol (61.2 mL, 0.661 mol) was then added slowly and portionwise. The mixture was heated at 40 C. to 45 C. for 1 hour, then cooled to 35 C. 2-amino-6-fluorobenzo-nitrile (50.0 g, 0.367 mol) was added and refluxed for 21 hours. The mixture was cooled to r.t., then ice (250 g), ice water (750 mL), and hexanes (1000 mL) was added. Insoluble solids were filtered out and the organic layer was separated. The aqueous layer was extracted once more with a mixture of diethyl ether (250 mL) and hexanes (250 mL). The combined organic layer was washed twice with a solution of citric acid (53 g) in water (500 mL), then washed with 80% brine (300 mL), then dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in methanol (500 mL), and the immiscible oil carried through from the sodium hydride suspension was separated off in a separatory funnel. The solvent was evaporated under vacuum, and the residue was washed with hexanes (250 mL), after which the product 2-amino-6-isobutoxybenzonitrile was obtained as a viscous oil (46 grams, yield: 66%). 1H NMR (400 MHz, DMSO-d6) delta 7.16 (t, J=8.0 Hz, 1H), 6.33 (d, J=8.0 Hz, 1H), 6.17 (d, J=8.0 Hz, 1H), 5.97 (s, 2H), 3.75 (d, J=7.2 Hz, 2H), 2.00 (m, 1H), 0.97 (d, J=6.8 Hz, 6H) ppm. MS 191 (MH+).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Amino-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 77326-36-4

A solution of 2-amino-6-fluorobenzonitrile (10.0 g) in H2S04 (75.0 mL) was stirred for 1.5 h at 65 C. Then the mixture was poured into ice and brought to pH = 9 by 20% NaOH aqueous solution, followed by the extraction with ethyl acetate three times. The combined organic layer were washed with brine and dried over Na2S04. It was filtered to remove insoluble matters and it was concentrated in vacuo to give compound 1-1 as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 77326-36-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; HIRABAYASHI, Tomokazu; KATSUNO, Mika; SMITH, Cameron James; SHERER, Edward; CAMPEAU, Louis-Charles; BALKOVEC, James; GREENLEE, William John; LI, Derun; GUO, Liangqin; CHAN, Tin Yan; CHEN, Yi-Heng; CHEN, Yili; CHACKALAMANNIL, Samuel; TAN, John Qiang; WO2014/99694; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts