Some common heterocyclic compound, 57053-02-8, name is Dimethyl 2-aminoisophthalate, molecular formula is C10H11NO4, 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. HPLC of Formula: C10H11NO4
2,6-Di(4-hydroxyheptan-4-yl)aniline Xlb (R2 = B). A suspension of fresh magnesium (20.9 g, 0.86 mol, 8.6 eq) in anhydrous THF (300 mL) was treated with the slow addition of a premade solution of n-propylbromide (69.5 mL, 0.77 mol, 7.7 eq) in anhydrous THF (300 mL) over 20 mm in maintaining the temperature below 40 DC. After 1.5 h at room temperature, the suspension was cooled down to 0 DC, causing theformation of a precipitate, and a premade solution of diester X (where R1 is methyl) (20.0 g, 0.10 mol, 1.0 eq) in dry THF (300 mL) was cannulated at 0 DC. The reaction was allowed to warm up to room temperature and was stirred for 2 h. The reaction was then cooled down to 0 DC and carefully quenched with sat. NH4CI solution (300 mL). The mixture was diluted in Et20 (400 mL) and washed with sat. NH4CI solution (2 x 200mL). The organic layer was then dried over anhydrous magnesium sulphate and concentrated under vacuum. The resulting brown crude solid (30.9 g) (Pure by 1H NMR) was then further purified by successive recrystallisation from pentane to give the pure diol XIb (26.6 g, 86%) as a white crystalline solid.1H NMR (400 MHz, CDCI3) 60.90 (12H, app t, J = 7.3 Hz, 4 x CH3), 1.08-1.23 (4H, m,4 x CH), 1.26-1.41 (4H, m, 4 x CH), 1.78-1.88 (4H, td, J = 12.5, 4.5 Hz, 4 x CH), 1.95-2.05 (4H, td, J =12.5, 4.5 Hz, 4 x CH), 4.24 (3H, vbs, NH2 + 2 x OH), 6.54 (1H, t, J =7.7 Hz, H), 6.89 (2H, d, J = 7.7 Hz, H?).13C {H} NMR (100 MHz, COd3) 6 14.5(4 x CH3), 17.2(4 x CH2), 41.2 (4 x CH2), 79.4(2 x C,-OH), 115.1 (CH/1), 126.5(2 x CH(nAr), 128.7(2 x CHOAr), 146.7 (CivNH2). HRMS (NSI+): found m/z [M + H]+ 322.2745, calcd for C20H36O2N 322.2741.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57053-02-8, its application will become more common.
Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; NOLAN, Steven P; MEIRIES, Sebastien; WO2014/108671; (2014); A1;,
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