Hydrochloric Acid → Chloride

Participants

Reaction Steps

To a pale brown suspension of 9-amino-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (11 g, 39.8 mmol) in con. HCl (25 mL) stirred at r.t. was added dropwise sodium nitrite (3.57 g, 51.8 mmol) in water (9 mL) at such a rate that the temperature of the reaction mixture would not exceed 45° C. (Ice bath!Slow addition!). Stirring continued for 5 h. The solution was poured into 120 mL of water and allowed to stand overnight in the refrigerator. The precipitate was collected by filtration, washed with water and dried to afford 7-carboxy-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-9-diazonium, Chloride (5 g, 15.45 mmol, 38.8% yield). LCMS: (M+H)+: 324.2.

Provenance & Evidence