18595-18-1

Methyl 3-amino-4-methylbenzoate(18595-18-1) is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Beige powder

Methyl 3-Amino-4-methylbenzoate(18595-18-1) is used as a reagent in the synthesis of perfluoroalkylated indoles which are very useful in drug development. It was also used in the preparation of 4-(pyrimidin-2-ylamino) benzamide derivatives which are designed as inhibitors of hedgehog signalling pathway (target of cancer treatment).

Methyl 3-amino-4-methylbenzoate(18595-18-1) can be used for:
To prepare the methyl 4-methyl-3-((4-(proparg-1-yloxy)benzyl)amino)benzoate, 4-proparg-1-yloxybenzaldehyde (16) and methyl 3-amino-4-methylbenzoate were reacted according to the method IA.
Synthesis of Methyl 4-methyl-3-((4-(2-methylthiazol-4-yl)benzoyl)amino)benzoate
Synthesis of 4-Methyl-3-((4-(2-methylthiazol-4-yl)benzoyl)amino)benzamide

Synthesis of methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1 (2H)-yl)-4-methylbenzoate
Synthesis of (5-Carbomethoxy-2-methylphenyl)(4-hydroxypheny)diazene: To a solution of 6N HC1 (6 mL) was added methyl 3-amino-4-methylbenzoate (1.62 g, 10.0 mmol). The solution was cooled in an ice-bath, and was diazotized by adding sodium nitrite (0.9 g, 12.0 mmol). To a cold solution of phenol in 21% aqueous NaOH solution (6 mL) was added diazotized solution slowly. After 20 min, the solution was acidfied by adding 4 N aqueous HC1 and was poured into the cold water, filtered, and washed with water. Recrystallization from ethanol gave the product (2.0 g, 74%) as red crystals, mp 181.3-182.2 °C.

ChEBI: Methyl 3-amino-4-methylbenzoate is a benzoate ester.

Synthesis of Methyl 3-amino-4-methylbenzoate(18595-18-1): 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)

3-Amino-4-methylbenzoic acid (60.5 g, 0.40 mol) was dissolved in anhydrous methanol (1.5 L), stirred and cooled to 5°C. The reaction was completed by the addition of thionyl chloride (103.6 g, 0.87 mol). Thionyl chloride (103.6 g, 0.87 mol) was added slowly dropwise, and after completion of the dropwise addition, the reaction was stirred and refluxed for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was concentrated under reduced pressure. The residue was diluted with ice water (1.2 L) and neutralized by adding 5% NaHCO3 solution to pH 7.5. The aqueous layer was extracted with ethyl acetate (3 × 600 mL), and the organic layers (2 × 500 mL) were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give methyl 3-amino-4-methylbenzoate (62.7 g, 94.9% yield) as a white solid.

[1] Patent: CN105693520, 2016, A. Location in patent: Paragraph 0184; 0185; 0186; 0187; 0188; 0189
[2] Patent: EP3067351, 2016, A1. Location in patent: Paragraph 0083; 0084
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2423 - 2435