Ethanol → HCID 178419957, compound

Reaction equation

C(O)C.C[N:5](C)/[CH:6]=[CH:7]/[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=O.O.[NH2:18]N>O>[NH:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:18]1

Participants

Procedure

To 50 mL absolute ethanol was added (E)-3-(dimethylamino)-1-(pyridin-4-yl)prop-2-en-1-one (20 g; Example 1, Step 1). When all solids dissolved, 6.33 mL hydrazine monohydrate was added dropwise with stirring. After 30 minutes an additional 1.1 mL hydrazine hydrate was added. After 2 hours the reaction was treated with water and the yellow solution was concentrated under vacuum until a slurry formed. The resulting solid product was collected by vacuum filtration, washed with water, and dried under high vacuum overnight to yield 15.27 g (93% yield) of product as off-white crystals. 1H NMR (CDCl3) was consistent with a tautomeric mixture of the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 146.4 by positive ESI.