Potassium Hydroxide → HCID 178477933, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-chlorobenzylidene)quinuclidin-3-one (35.0 g), potassium hydroxide (15.0 g) and hydrazine hydrate (11.0 cm3) in ethylene glycol(100 cm3) was heated at 110° C. for 15 minutes to produce a dear, dark brown solution. Hydrazine hydrate and water were distilled from the solution over 1 hour at 110° C. to 195° C. The brown solution was then heated at reflux for 3 hours. The mixture was cooled to room temperature and diluted with water (300 cm3). The resulting white precipitate was collected and washed with water (500 cm3) and ethyl acetate (200 cm3). The white powder was dried in vacuo to give the title compound (31.5 g, 85%), m.p. 174°-176° C.; δH (250 MHz; d6 -DMSO) 1.52 (2H, apparent qd, J=12 and 4, 2×NCH2CHAHB), 1.85 (2H, apparent d, J=10, 2×NCH2CHAHB), 2.56 (2H, apparent td, J=12 and 2, 2×NCHAHB), 2.71 [1H, tt, J=8.1 and 4.5, (CH2)2CH], 2.99 (2H, apparent d, J=12.1, 2×NCHAHB), 6.48 (1H, s, N=C--CH=C), 7.44 (2H, d, J=8.6, 2×ArH o to Cl; and 7.79 (2H, d, J=8.6, 2×ArH m to Cl); δC (90 MHz; d6 -DMSO) 39.9 (t), 34.2 (d), 46.2 (t), 98.9 (d), 126.8 (d), 128.7 (d), 131.7 (s), 132.4 (broad, s), 147.5 (broad, s) and 151.1 (broad, s); m/z (CI+, NH3) 262 (M+ +H; 60%) and 139 (100).

Provenance & Evidence