1-Bromopentane → HCID 19363268, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-4-nitrobenzoic acid (5 g, 27.4 mmol), DMF (40 ml), potassium carbonate (13.8 g, 100 mmol) and pentyl bromide (8.7 ml, 70 mmol) were mixed, and this solution was stirred at 100° C. for 1.5 hours. The reaction mixture was filtered to remove the inorganic salt, and DMF was evaporated under reduced pressure. Ethyl acetate (100 ml) was added to the obtained residue, and the mixture was washed 3 times with saturated brine (30 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Ethanol (150 ml) and 10% palladium carbon catalyst (0.5 g) were added to the obtained residue, and the mixture was stirred at room temperature for 5.5 hours in a stream of hydrogen. The palladium-carbon catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=5/1) to give pentyl 4-amino-3-pentyloxybenzoate (5.72 g, 70% in 2 steps) as a pale-yellow oil.

Provenance & Evidence