1,1-Dimethylhydrazine → HCID 86747025, compound

Participants

Reaction Steps

N,N-Dimethylhydrazine (10.90 mL, 0.14 mol) was added dropwise over 15 min to (E)-4-methoxy-2-butenal (13.06 g, 0.13 mol) while cooling the reaction with an ice bath. The bath was then removed and the mixture stirred for 1.5 h at ambient temperature. Calcium chloride (20 g) was added to the reaction, let set for 15 min, and the product decanted. Distillation (bp 102°-110° C., 25 mm Hg) of the oil through a 10 cm Vigreaux column provided pure (E)-4-methoxy-2-butenal N,N-dimethylhydrazone (17) (14.45 g, 78%): IR (neat) 2850, 2820, 1560, 1465, 1445, 1375, 1270, 1120, 1030, 970 cm-1 ; 1H NMR (CDCl3) δ 2.80 (s, 6H), 3.26 (s, 3H), 3.93 (dd, 2H, J=6.2, 1.2 Hz), 5.74 (dt, 1H, J=15.8, 6.2 Hz), 6.31 (ddt, 1H, J=15.8, 8.9, 1.2 Hz), 6.92 (d, 1H, J=8.9 Hz); Anal. calcd for C7H14N2O: C 59.05, H 10.07, N 19.52; found C 59.13, H 9.92, N 19.70.

Provenance & Evidence