Related Products of 77326-36-4, 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.
It was prepared as described for 8. Starting from freshly sublimed 2-amino-6-fluorobenzonitrile (918 mg, 6.75 mmol) in 1,2-dichloroethane (8 mL) and enone 7 (R9 = allyl) (800 mg, 4.50 mmol) in 1,2-dichloroethane (40 mL), and heating the reaction mixture under reflux for 16 h, a crude product (1.75 g) was obtained and subjected to column chromatography [silica gel (62 g), CH2Cl2/MeOH/25% aqueous NH4OH mixtures as eluent]. On elution with CH2Cl2/MeOH/25% aqueous NH4OH 99:1:0.05, huprine 11 (762 mg, 58% yield) was obtained as a beige solid.A solution of huprine 11 (762 mg, 2.59 mmol) in MeOH (6 mL) was treated with 1.81 N methanolic HCl (4.3 mL, 7.78 mmol) and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 15:2 (34 mL), 11·HCl was obtained as a light brown solid (570 mg), mp >300 C (dec.) (AcOEt/MeOH 15:2). IR (KBr) nu 3600-2400 (max at 3394, 3314, 3201, 3166, 3071, 3020, 2926, 2902, 2829, 2774, 2669, 2604, C-H, N-H, and N+-H st), 1640, 1593, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 1.98 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.05 (br d, J ? 17.5 Hz, 1H, 10-Hendo), 2.10 (dm, J = 12.5 Hz, 1H, 13-Hanti), 2.51 (ddm, J = 17.5 Hz, J’ = 5.5 Hz, 1H, 10-Hexo), 2.63 (d, J ? 7.0 Hz, 2H, 9-CH2-CHCH2), 2.83 (m, 1H, 7-H), 2.88 (ddd, J = 18.0 Hz, J’ = J = 2.0 Hz, 1H, 6-Hendo), 3.22 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.40 (m, 1H, 11-H), 4.86 (s, NH2 and NH+), 4.88-4.91 (complex signal, 2H, 9-CH2-CHCH2), 5.63 (dm, J = 7.0 Hz, 1H, 8-H), superimposed in part 5.65 (ddt, J = 17.0 Hz, J’ = 10.0 Hz, J = 7.0 Hz, 1H, 9-CH2-CHCH2), 7.34 (ddd, J = 14.0 Hz, J’ = 8.5 Hz, J = 1.0 Hz, 1H, 2-H), 7.57 (ddd, J = 8.5 Hz, J’ = J = 1.0 Hz, 1H, 4-H), 7.83 (ddd, J = J’ = 8.5 Hz, J = 6.0 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 27.2 (CH, C11), 28.1 (CH, C7), 29.3 (CH2, C13), 34.0 (CH2, C10), 35.9 (CH2, C6), 42.5 (CH2, 9-CH2-CHCH2), 107.4 (C, d, J = 12.1 Hz, C12a), 112.2 (CH, d, J = 23.0 Hz, C2), 115.8 (C, C11a), 116.3 (CH, C4), 116.4 (CH2, 9-CH2-CHCH2), 125.7 (CH, C8), 135.0 (CH, d, J = 11.5 Hz, C3), 137.2 (CH, 9-CH2-CHCH2), 137.3 (C, C9), 140.7 (C, C4a), 152.9 (C) and 155.4 (C) (C5a and C12), 161.2 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H19FN2·HCl (330.83): C, 68.98; H, 6.09; N, 8.47; Cl, 10.72. Found: C, 68.65; H, 6.20; N, 8.35; Cl, 11.14.
Statistics shows that 2-Amino-6-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 77326-36-4.
Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts