The common heterocyclic compound, 7379-35-3, name is 4-Chloropyridine hydrochloride, molecular formula is C5H5Cl2N, 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. 7379-35-3
Prepare a solution of 12.4 kg (110.7 mol) potassium tert-butoxide in 23.6 kg NMP, stir the suspension at 20 C until a clear solution is obtained (Solution A). Prepare a second solution of 5.84 kg (27.7 mol, assay 82.6 percent) N-propyl-1H-indol-1 amine and 4.36 kg (29.1 mol) 4-chloropyridine hydrochloride in 15 kg NMP (Solution B). Add solution A to solution B while maintaining the temperature at 20 C. Stir for lh and check for completion of reaction. The reaction mixture is quenched in 135 kg water. Adjust pH value of the solution to about 2 with HC1 (30 percent) and extract with 20 kg n-heptane twice. Discard organic layer. Adjust pH value of the aqueous layer tol2 with NaOH (33 percent) and extract with 16 kg n-butylacetate twice. Discard aqueous layer. Wash organic layer with 23 kg of water. Add 10.8 kg methanolic HC1 (29.9 mol, assay 10.1percent) to the organic layer at 20 C. After crystallization cool the mixture to 5 C, filter the product and wash with n- butylacetate. Dry under vacuum at 80 C in a tray dryer. This will result in 5.8 kg indol-1-yl-propyl-pyridin-4-yl-amine hydrochloride (yield 73percent) as a white to beige solid. 1H-NMR (400 MHz, DMSO-d6, TMS) [5, ppm]: 0.94 (t, 3H, CH3), 1.62 (m, 2H, CH2), 4.05 (dm, 2H, CH2), 6.74 (d, 1H, arom. ), 7.19 (m, 1H, arom. ), 7.28 (m, 1H, arom. ), 7.30 (d, 1H, arom. ), 5.8-7. 6 (s v br, 2H, arom. ), 7.63 (d, 1H, arom. ), 7.70 (d, 1H, arom. ), 8.43 (d br, 2H, arom. ), 15. 2 (s br, 1H, NH+). MS (ES+): 252 [M++H, free base]
The synthetic route of 7379-35-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2005/35496; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem