Sodium Chloride → HCID 86692166, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL one-neck round-bottom flask was charged with 250.0 mg (0.24 mL, 1.825 mmol, 1.04 eq) 4-ethoxyaniline which was dissolved in 3.1 mL acetic acid at 10° C. (ice bath). To this cooled solution 128.0 mg (1.861 mmol, 1.06 eq) NaNO2 in 0.5 mL conc. H2SO4 were added and the reaction mixture was stirred at 10° C. for 1 h. In a second 25 ml one-neck round-bottom flask 288.6 mg (0.24 mL, 1.755 mmol, 1.0 eq) ethyl-4-chloro-3-oxobutanoate were dissolved in a mixture of 1.3 mL acetic acid and 2.6 mL water and cooled to 0° C. (ice bath+NaCl). After one hour stirring at 10° C. the generated solution of the diazonium salt was given to the second solution at 0° C. and stirred for further 15 min at this temperature. An aqueous solution of 1.58 g (19.305 mmol, 11 eq) NaOAc in 3.0 mL water was added to the reaction mixture at 0° C. and the product precipitated. Stirring at rt over night, filtration, washing with a small amount of water and drying under high pressure yielded the crude product which was used in the next reaction step without further purification.

Provenance & Evidence