Sodium hydride → HCID 54556570, compound

Participants

Reaction Steps

Following the alkylation procedure described in Example 608, Part D, 2.0 g (12 mmole) of 1,5-diazafluorene, 4.68 g (29 mmole) of 4-picolylchloride, 1.44 g (30 mmole) of 50% sodium hydride were heated at 55 in 10 ml tetrahydrofuran and 25 ml benzene until TLC (ethyl acetate-methanol-90:10) showed appearance of product (Rf 0.065) and disappearance of starting diazafluorene (Rf 0.28). Crude product triturated with ether to yield 2.90 g, m.p. 133°-137°. This was flash chromatographed with ethyl acetate and recrystallized from benzene using charcoal to decolorize. Yield 2.4 g, m.p. 139.8°-140.9°. Rf 0.16 (ethyl acetate-methanol 90:10). NMR (200 MHz,CDCl3) δ 3.397-3.718(dd,4H,(--CH2 --pyridyl); 6.450-6.475(d,4H,β-pyridyls); 7.240-7.324(m, 2H,the 3- and 7- H's of the 1,5-diazafluorene, each meta to one of the nitrogens); 7.802-7.808 (d, 1H,8-H of diazafluorene); 7.879-7.885(d,1H,4---H of diazafluorene); 8.097-8.122 (d,4H, α-pyridyls); 8.451-8.476(d, 1H,2-H of diazafluorene); 8.741-8.763(d,1H,6-H of diazafluorene). ##STR1032## Difference=0.0003 for C23H18N4.

Provenance & Evidence