ChemicalBook CAS DataBase List 4-Amino-3-methoxybenzoic acid

4-Amino-3-methoxybenzoic acid synthesis

5synthesis methods

Product Name:4-Amino-3-methoxybenzoic acid
CAS Number:2486-69-3
Molecular formula:C8H9NO3
Molecular Weight:167.16

41608-64-4 Synthesis

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2486-69-3
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Yield:2486-69-3 96.35%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran;methanol at 25; for 12 h;Inert atmosphere;

Steps:

A45 Preparation of 4-amino-3-methoxybenzoic acid
To a solution of methyl 4-amino-3- methoxybenzoate (4.5 g, 23.59 mmol, 1 eq.) in MeOH (45 mL), water (15 mL), and THF (15 mL) was added LiOH (4.95 g, 117.97 mmol, 5 eq.) in one portion at 25 °C under N2. The mixture was stirred at 25 °C for 12 h. TLC analysis (PE:EtOAc = 3:1, Rf = 0) showed that the reaction was complete. The mixture was concentrated under reduced pressure at 40 °C. The residue was poured into water (50 mL) and stirred for 1 min. The aqueous phase was extracted with EtOAc (30 mL x 3).2 N HCl was added to the aqueous phase to adjust the pH of the solution to 2. The aqueous phase was filtered and concentrated in vacuo to afford the desired product (4 g, 22.73 mmol, 96.35% yield) as a light yellow solid.

References:

PMV PHARMACEUTICALS, INC. WO2021/61643, 2021, A1 Location in patent:Paragraph 0289

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