4-Nitrobenzoyl chloride → HCID 136005808, compound

Participants

Reaction Steps

To a pyridine solution of 2.2 g (10 mmol) of the compound obtained in Example 32, 2.2 g (13 mmol) of p-nitrobenzoyl chloride was added, and the mixture was stirred at room temperature for 1.5 hours. Then, the reaction mixture was distilled under reduced pressure, and an aqueous solution of sodium hydrogen carbonate was added to the residue, followed by extracting the mixture with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. To the residue, 30 ml of methanol and 400 mg of 10% palladium carbon were added. The mixture was stirred for 8 hours in an atmosphere of hydrogen at room temperature and atmospheric pressure. Then, the catalyst was removed by filtration, and the filtrate was distilled under reduced pressure. To the residue, 80 ml of ethanol and 40 ml of a 1M aqueous solution of sodium hydroxide were added, followed by heating the mixture under reflux for 5 hours. Then, the reaction mixture was cooled to room temperature, diluted with water, and extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain 960 mg (30%) of the captioned compound.

Provenance & Evidence