3556-83-0

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-METHOXY-4-METHYLBENZOATE is used as a reactant for the preparation of antimalaria drugs, specifically those that consist of the 4-aminoquinoline pharmacophore of chloroquine combined with clotrimazole-based antimalarials. Its unique chemical properties contribute to the development of effective treatments against malaria, a disease that affects millions of people worldwide.

Preparation

Methyl 3-methoxy-4-methylbenzoate is synthesized by the following steps:A mixture of methyl 3-hydroxy-4-methylbenzoate 36 (25 g, 0.151 mol), ?Me2SO4 (28.3 ml, 0.386 mol), anhydrous K2CO3 (103.5 g, 0.75 mol) was ?refluxed in acetone for 2 hours. K2CO3 was filtered off, washed ?thoroughly with acetone. The filtrates were combined and concentrated, ?the residue was redissolved in EtOAc washed with water, dried ?(anhydrous Na2SO4), filtered and concentrated in vacuo to furnish a white solid (19.52 g). ?Yield : 72%.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 33, p. 1771, 1990 DOI: 10.1021/jm00168a036

InChI:InChI=1/C10H12O3/c1-7-6-8(10(11)13-3)4-5-9(7)12-2/h4-6H,1-3H3

Upstream product

• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 7151-68-0 3-methoxy-p-toluic acid 
• 67-56-1 methanol 
• 922-67-8 propynoic acid methyl ester 
• 108298-28-8 4-Methoxy-5-methyl-2H-pyran-2-on 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 104901-43-1 methyl 3-bromo-4-methylbenzoate 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 62454-72-2 4-methyl-3-sulfobenzoic acid 
• 584-08-7 potassium carbonate 
• 121-44-8 triethylamine 

Downstream Products

• 7151-68-0 3-methoxy-p-toluic acid 
• 86239-03-4 ethyl 3-methoxy-4-methylbenzoate 
• 4685-51-2 4-(chloromethyl)-2-methoxy-1-methylbenzene 
• 140462-31-3 (+/-)-faveline methyl ether 
• 79236-96-7 2-methoxy-4-(hydroxymethyl)-3-methoxybenzoate 
• 74733-24-7 4-formyl-3-methoxybenzoic acid methyl ester 
• 188244-57-7 5-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-51-1 6-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-60-2 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-67-9 7-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-20-6 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-3-methyl-4-oxo-1,4-dihydroquinoline 
• 188244-74-8 6-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-19-3 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-2-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-37-5 3-Methoxy-4-(7-nitro-4-oxo-4H-quinolin-1-ylmethyl)-benzoic acid 

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