
Methyl 2-amino-4,5-dimethoxybenzoate synthesis
- Product Name:Methyl 2-amino-4,5-dimethoxybenzoate
- CAS Number:26759-46-6
- Molecular formula:C10H13NO4
- Molecular Weight:211.21

26791-93-5

26759-46-6
General procedure for the synthesis of methyl 2-amino-4,5-dimethoxybenzoate from methyl 4,5-dimethoxy-2-nitrobenzoate: 1.9 g (7.2 mmol) of methyl 4,5-dimethoxy-2-nitrobenzoate and 0.2 g of palladium-carbon catalyst were added to a 100 mL round-bottomed flask and dissolved in 50 mL of methanol. Hydrogen was passed into the reaction system and the reaction mixture was stirred at room temperature for 24 hours. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the brown solid catalyst was removed by filtration. The product was separated and purified by column chromatography (eluent ratio: petroleum ether:ethyl acetate = 10:1, V/V) to afford 1.51 g of the white solid target compound in 88.7% yield with a melting point of 91-93°C. The product was purified by column chromatography (eluent ratio: petroleum ether:ethyl acetate = 10:1, V/V).

26791-93-5
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26759-46-6
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Yield:26759-46-6 97%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in ethyl acetate at 25; under 775.743 Torr; for 16 h;
Steps:
1.3
Step 3: A mixture of c (1.0 g, 4.1 mmol, 1.0 eq) and Pd/C (10% wt., 300 mg) in EtOAc (15.0 mL) was stirred at 25 oC under H2 (15 psi) atmosphere for 16 hours. The reaction mixture was filtered through celite and the filter cake washed with EtOAc (20 mL). The filtrate was concentrated to afford d (840 mg, 97%) as a light yellow solid.1H NMR (400 MHz, DMSO- d6): d 7.12 (s, 1H), 6.45 (s, 2 H), 6.36 (s, 1H), 3.74 (s, 6 H), 3.64 (s, 3 H).
References:
SILICON SWAT, INC.;ALLEN, Bryce K.;CHAMBERLAIN, Brian T.;DWIGHT, Timothy A.;HUANG, Huang;LIN, Zhixiong;MARINO, Kristen A.;NIU, Deqiang;SHECHTER, Sharon;SWANN, Steven WO2020/232375, 2020, A1 Location in patent:Page/Page column 99-100

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26759-46-6
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