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ChemicalBook CAS DataBase List Methyl 3-amino-4-methylbenzoate
18595-18-1

Methyl 3-amino-4-methylbenzoate synthesis

6synthesis methods
Synthesis of Methyl 3-amino-4-methylbenzoate: Nitro ester Methyl 4-methyl-3-nitrobenzoate (80 g, 0.410 mol) was subjected to hydrogenation in a Parr shaker in MeOH using Raney Ni as the catalyst (5 g, 20 mol %) at 50 psi for 8 hours. The catalyst was filtered off, washed thoroughly with MeOH and the combined filtrates concentrated under reduced pressure to furnish a yellow solid (65.0 g). Yield : 96% Mp : 114-5°C (lit.14 Mp 116°C)
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Yield:18595-18-1 97%

Reaction Conditions:

with dichloro sulfoxide in methanol; for 4 h;Cooling with ice;

Steps:

1.2. Methyl 3-amino-4-methylbenzoate (2)

In a round bottom flask were added 3-amino-4-methylbenzoic acid 1 (1.00 g, 6.62 mmol) and anhydrous MeOH (25 mL). The solution was cooled in an ice bath and SOCl2 (1.71 g, 14.4 mmol, 1.05 mL) was added dropwise. The solution was stirred and refluxed for 4 h and then concentrated under reduced pressure. A saturated aqueous NaHCO3 solution (40 mL) was added and the mixture was extracted with EtOAc. Combined organic phases were dried over MgSO4. After evaporation, compound 2 (1.06 g, 6.42 mmol, 97%) was obtained as a beige powder.

References:

Auvert, Etienne;Aesoy, Reidun;Giraud, Francis;Herfindal, Lars;Anizon, Fabrice;Moreau, Pascale [Bioorganic and Medicinal Chemistry Letters,2022,vol. 73,art. no. 128914]

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