ChemicalBook CAS DataBase List 2-AMINOTEREPHTHALIC ACID

2-AMINOTEREPHTHALIC ACID synthesis

7synthesis methods

Product Name:2-AMINOTEREPHTHALIC ACID
CAS Number:10312-55-7
Molecular formula:C8H7NO4
Molecular Weight:181.15

610-29-7

10312-55-7

General procedure for the synthesis of 2-aminoterephthalic acid from 2-nitroterephthalic acid: in typical experiments, a mixture of nitroaromatic compounds (1.0 mmol), ammonium formate (3.3 mmol, 208 mg, 1.1 eq.), palladium catalyst (10% Pd/C, 2 mol%, 21 mg), and silicon dioxide (175 mg) was ball-milled in the presence of anhydrous methanol (η= 0.25 μL/mg) was ball-milled for 90 min in the presence of anhydrous methanol (η= 0.25 μL/mg). Upon completion of the milling, a small amount (~1 mg) of the crude reaction mixture was suspended in methanol and analyzed by thin-layer chromatography (TLC, usually using a solvent mixture of dichloromethane: methanol = 20:1 as eluent). The crude product was placed in a well-ventilated fume hood overnight, then suspended in methanol and filtered through a Büchner funnel. The filtrate is evaporated to give the target product 2-aminoterephthalic acid. If necessary, the final product can be further purified by column chromatography.

610-29-7 Synthesis

610-29-7
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$9.00/5g

10312-55-7
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$7.00/1g

Yield:10312-55-7 99%

Reaction Conditions:

with palladium 10% on activated carbon;ammonium formate;silica gel in methanol; for 1.5 h;Milling;

Steps:

2. General procedure for the mechanochemical reduction of nitroarenes

General procedure: In a typical experiment, a mixture of nitroarene compound (1.0 mmol),ammonium formate (3.3 mmol, 208 mg, 1.1 equivalent), palladium catalyst (10 % Pdon activated carbon, 2 mol%, 21 mg) and silica (175 mg) was ball milled in thepresence of dry methanol (η = 0.25 μL mg-1) for 90 minutes. After milling, a smallsample (≈ 1 mg) of the crude reaction mixture was suspended in methanol andimmediately analyzed by TLC (typically using dichloromethane : methanol = 20 : 1mixture as an eluent). The crude mixture was left in a well ventilated hood overnight,suspended in methanol and filtered over a Büchner funnel. Evaporation of the filtrateafforded the desired amino-derivative. If necessary, the final product was purified bycolumn chromatography.

References:

Portada, Tomislav;Margeti?, Davor;?trukil, Vjekoslav [Molecules,2018,vol. 23,# 12,art. no. 3163] Location in patent:supporting information