18595-18-1, A common compound: 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
The requisite 4-methyl-3-(pyridine-4-carbonylarnino)benzoic acid starting material (Step3) was prepared as follows: Step 1: Preparation of methyl 4-methyl-3-(pyridine-4-carbonylamino)benzoate; A solution of methyl 3-amino-4-methyl-benzoate (8.255 g, 50 mmol) and TEA (13.9 mL, 100 mmol, 2 eq) in DCM (200 mL) was cooled in an ice-bath and pyridine-4-carbonyl chloride (9.795 g, 55 mmol, 1.1 eq) was added portionwise as a solid. The reaction mixture was stirred for 30 mins, the ice-bath was removed, and stirring continued for a further 1 hr. Extra acid chloride (2 g, 0.2 eq) was added and the reaction mixture stirred a further 1 hr. It o was then diluted with more DCM and the resulting solution washed sequentially with water (twice), saturated sodium bicarbonate solution, and brine. At this stage a solid started to precipitate out, so more DCM was added. The solid precipitate (2 g) was isolated by titration and the filtrate dried (PS Paper) and evaporated to give a solid (10.7 g). The two fractions were identical (NMR, LCMS) and combined to give the title compound (12.7 g) 5 as a yellow solid, 1H NMR (400.132 MHz, DMSO) 62.33 (s, 3H),3.86 (s, 3H),7.46 (d, 1H),7.79 (d, 1H),7.87 -7.94 (m, 2H),7.98 – 8.05 (m, 1H),8.81 (d, 2H),10.35 (s, IH), m/z 271 (M+H+) 269 (M-H”).
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, Methyl 3-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59214; (2008); A1;,
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