Hydrochloric Acid → 4-(Hydroximinomethyl)cinnoline

Reaction equation

[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.Cl.[N:13](OCCCC)=[O:14]>C(O)C>[N:13](=[CH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1)[OH:14]

Participants

Procedure

A solution of 1.44 g of 27A in 3 ml of absolute ethanol was added drop-by-drop over 3 minutes to 3.4 ml of stirred absolute ethanol containing 0.9 g of anhydrous hydrogen chloride, at 0° C. The resulting mixture was stirred for 30 minutes, then a solution of 1.03 g of butyl nitrite in 2 ml of absolute ethanol was added drop-by-drop over 3 minutes at 0° C. The mixture was stirred for 30 minutes at 0° C., for 4 hours at room temperature, then stored in a refrigerator overnight. A precipitated solid was collected, washed with a small amount of water, mixed with a saturated potassium bicarbonate solution, and filtered. Recrystallization from water gave 4-(hydroximinomethyl)cinnoline (27B), as a solid, m.p.: 223° C. (with decomposition).