Ammonia → HCID 20334397, compound

Participants

Reaction Conditions

Reaction Steps

A 500 ml, three-necked, round bottom flask was fitted with mechanical stirrers, thermometer, Dry Ice/acetone reflex condenser (with KOH drying tube) and addition funnel. To the flask was added 210 ml of liquid ammonia and 8.7 g (0.035 mole) of 3-bromocarbazole (from Example 16A). To this mixture was added 1.52 g (0.039 mole) of sodium amide at -33° C. The resulting mixture was stirred mechanically at -33° C. for 3 hr. The mixture was then cooled to -55° C. and 5.9 g (0.049 mole) of 3-bromo-1-propyne was added dropwise over a period of 20 min. After stirring at -55° C. for an additional 5 hr, the ammonia was allowed to evaporate overnight. The residue was extracted three times with 300 ml portions of benzene. Concentration of the combined benzene extractants gave 9.5 g (95% yield) of light yellow powder, m.p. 142°-149° C. Recrystallization from methanol gave colorless needle crystals, m.p. 155°-157° C. I.R. (KBr pellet) in cm-1 : 3300 (C≡CH), 3070 (Ar--H), 2940 (CH), 2140 (C≡C), 1630+1600 (C=C), 1455+1330 (CN), 800+740+720 (Ar), 680+660 (C≡CH). Anal: calculated for C15H10NBr: C, 63.40%; H, 3.55%; N, 4.93%; found: 63.37%; H, 3.35%; N, 4.83%.

Provenance & Evidence