1,3,5-Benzenetriol, 2-amino- synthesis

Yield:-

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20;

Steps:

1

Example 1 : Chemical synthesis of compound 1 D; Nitrophloroglucinol (1 g, 6.5 mMol) was dissolved in 10 ml of methanol and hydrogenated in a hydrogen atmosphere in the presence of 0.1 g of 10% Pd/C overnight at room temperature. The solvent was removed by evaporation an the residue was dissoved in 12 ml of dimethylformamide. 2-chlor-5-nitrobenzoic acid (1.2 g; 6 mMol), 1.7 g of K2CO3, 0.18 g of copper powder and 0.18 g of CuCI were added and the mixture was refluxed for 3 hours. After cooling to room temperature, 12 ml of concentrated HCI and 120 ml of water were added, and the product was extracted with 120 of ethylacetate. The organic phase was dried over Na2SO4 and evaporated. The product was dissolved in 12 ml of methanol; 0.1 g of palladium (10% ob charcoal) was added and hydrogenated in a hydrogen atmosphere overnight at room temperature. The catalyst was removed by centrifugation, and the solvant was evaporated to obtain compound 1 D.

References:

WO2010/66912,2010,A2 Location in patent:Page/Page column 30